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Патент USA US2136401

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Patented Nov. 15, 1938
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2,136,401
UNITED STATES PATENT. OFFICE
ACYL COll?’OUNDS OFTCYANHYDRINS OF
THE ET'IO - GHOLANE AND‘ ETIO-ALLO
CHOLANE
SERIES ANDI A METHOD‘ OF'
PRODUCING THE SAME,
'
_Lothar Strassberger, Berlin-Wilmersdorf, Ger
many, assignor to. Schering-Kahlbaum A; G.,
Berlin, Germany, a corporation of Germany
No Drawing. Application ‘February 27,‘ 1937, Se
rial No. 128,138. In'Germany MarchZ, 1936
9 Claims. (01'. 260-397)
This invention relates to acyl compounds of
cyanhydrins of compounds of the etio-cholane
'
Ewamplcz
-
and etio-allo-cholane series and a method of
producing the 58mm
-
'.
5 gram-S of androstenolone acetate cyanhydnn
aretreated as described in Example 1.
The process for the manufacture of cyanhy_
There I
is thus obta1ned the same androstenolone cyan-
5
drins is described in ‘the copending, application
Serial No. 58,754 and consists in bringing saturated or unsaturated etio-cholanones or etio-
hydrin diaceta'te"
>
‘
' Example 3
'
allocholanones into reaction with hydrocyanic
acid_
According to- the invention, these cyanhydrins
by treatment with such substances which serve
as reagents on alcoholic hydroxyl groups and thus
0-5 gram of trans-androsterone cyanhydrin is
treated according to Example lwith 3 cos. of 10
acetic anhydride. There is obtained the corre
Sponding (1134061581176 in a yield of about 75% 0f the
theory
form esters, as, for example, acid anhydrides,
acid chlorides, cyanic acid, its isomers and derivatives, such as phenyl isocyanate and the like,
are converted into the corresponding acyl derivatives, which in contradistinction to the cyan-
v '
Instead ofacetic anhydride also other acylat
ins agents can be employed, as, for example, ben- '15
Zoyl chloride, propionic acid anhydride, succinic
'
acid anhydride and-the like.
A150 the IeaCtioIl is 1101? limited '00 the Cyan
hydrins are characterized by great stability,
The new acyl compounds are likewise intended
to ?nd application as intermediate products for
, hydrins of the androstenolone compounds. Thus
in addition, for example, androstenolones and ‘20
also their esters and ethers or their other deriva~
the manufacture of substances of high physiological activity.
The reaction may, for example, be illustrated
in detail by the following scheme for the cyanhydrin of androstenolone acetate:
tiVeS with Converted hydroxyl groups, in which
these hydroxyl groups can easily be restored by
hydrolysis, can be employed as Starting materials.
Also among other things it may be of advantage 25
to treat the cyanhydrins with such acylating
0113
.
/\
CH3 ‘
\/
omooo-
ON
l/
CH3
OH
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000011,
,0
CH3
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+oH3oo\ o —>
\/ CHSCO/
N
o
'
\
35
CHsCO
The following examples illustrate the invention:
Exampze 1
.
agents as form mixed esters of the diol com
pounds, that is to say therefore as starting ma
terials such esters are employed, the acid radical 40
of which is different from the: acid radical em
5 grams of androstenolone cyanhydrin are
heated with 30 cc. of acetic anhydride ?rst for
one hour to 100-110° C. and thereupon for a further hour to 130-140° C. The excess of acetic
anhydride is distilled off in vacuum, and the
residue recrystallized from methanol. There is
ployed for the acylation. The reaction can be
carried out by customary methods as is known
for acylations; thus, the process can be conducted 45
in the presence of solvents, catalysts and the like.
The term “cholanone” as employed herein em
braces not only the saturated but also the nuclear
thus obtained the androstenolone cyanhydrin diacetate in the form of colorless crystals of M. P.
1y unsaturated compounds.
Of course, many changes and variations in the
210° C.
reaction conditions, the agents used and the like 50 '
2
7.“,
2,186,401
may be employed by those skilled in the art in sis, is reconvertible into the hydroxy group and
accordance with the principles set forth herein _ is in the 3-position, and Ac an acyl group.
7. An acyl compound of the cyanhydrin of the
and in the claims annexed hereto.
etio-cholane series having the general formula
What I claim is:
C19H27(OAc) (CN) X and the structural formula
1. Process for the manufacture of acyl com
pounds of cyanhydrins of the etio-cholane and
etio-allo-cholane series, wherein the cyanhydrins
5
are treated with such substances as will react
on tertiary alcoholic hydroxyl groups and there
10 by form esters.
2. Process as claimed in claim 1, in which the
starting material comprises a cyanhydrin of a
member of the group consisting of androsteno
lone and its derivatives, wherein the hydroxyl
15
15 group has been substituted by a group which can
be replaced by the hydroxyl group.
3. Process as claimed in claim 1 in which the
esterifying agent is a member of the group con
sisting of acid anhydrides, acid chlorides, and
20 cyanic acid, its isomers and derivatives, includ
ing phenyl-isocyanate.
4. Process for the manufacture of acyl com
pounds of cyanhydrins of the etio-cholane and
etio-allo-cholane series, which comprises react
25 ing a cyanhydrin of the etio-cholane and etio
allo-cholane series With an acylating agent in the
wherein X indicates a group that, upon hydroly
sis, is reconvertible into the hydroxy group and
is in the 3-position, and Ac an acyl group.
8. A diacetyl compound of trans-androsterone
cyanhydrin having the general formula
20
C19H29(O acety1)2(CN)
and the structural formula
CH;
presence of a solvent and of a catalyst.
CH3 \
5. An acyl compound of the cyanhydrins of the
etio~cholane and etio-allo-cholane series having
30 the general formula CmI-IMOAc) (CN) X, wherein
n indicates 2'? or 29, X a group that, upon hy
drolysis, is reconvertible into the hydroxy group
and is in the 3-position and Ac an acyl group.
6. An acyl compound of the cyanhydrin of the
35 etio-cholane and etio-allo-cholane series having
the general formula C19I-I29(OA0) (CN) X, and the
structural formula
OCOCH:
CHaCOO-—
.
a
V
30
9. A diacetyl compound of androstenolone cy
anhydrin having the general formula
C19H27(O acetyl) 2(CN)
35
and the structural formula
cm
0 o 0 CH;
/
40
CN
40
CH3
01150 0 0_(\ \
45
wherein X indicates a group that, upon hydroly
LOTI-IAR S'I'RASSBERGER.
45
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