Methoxyacetic Acid → HCID 53769477, compound

HRID 262967Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C:5](=[CH:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:22])[CH:4]=1.[CH3:23][O:24][CH2:25][C:26]([OH:28])=[O:27]>>[OH:22][C@@:12]1([C@:13]2([CH3:14])[C@H:9]([C@H:8]3[C@H:17]([CH2:16][CH2:15]2)[C@:18]2([CH3:21])[C:5]([CH:4]=[C:3]([O:2][CH3:1])[CH2:20][CH2:19]2)=[CH:6][CH2:7]3)[CH2:10][CH2:11]1)[CH:25]([O:24][CH3:23])[C:26]([OH:28])=[O:27]

Participants

Reactant 2

HCID 12251Methoxyacetic Acid

HCID 926873-Methoxyandrosta-3,5-dien-17-one

Product 1

HCID 53769477HCID 53769477, compound

Procedure

Under the conditions described in Example 1, 15 g. of 3-methoxy-3,5-androstadien-17-one is reacted with the lithium enolate of the methyl ester of methoxyacetic acid. After recrystallization of the crude product from methylene chloride/ether, 17.8 g. of the methyl ester of 17β-hydroxy-3,20-dimethoxy-3,5-pregnadiene-21-oic acid is obtained, m.p. 182°-185°.

Workup

customAfter recrystallization of the crude product from methylene chloride/ether, 17.8 g

Sources & evidence

ORD record: ord-ca6df5fe70e240dd98218d17f6505a49
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04155923

Reaction notes

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