Methoxyacetyl chloride → 11beta,17-Dihydroxy-21-methoxyacetoxy-6alpha-methyl-4-pregnene-3,20-dione

HRID 1903063Notes

Reaction equation

[OH:1][C@H:2]1[CH2:22][C@@:21]2([CH3:23])[C@@H:13]([CH2:14][CH2:15][C@:16]2([OH:24])[C:17](=[O:20])[CH2:18][OH:19])[C@H:12]2[C@H:3]1[C@:4]1([CH3:27])[C:9]([C@@H:10]([CH3:25])[CH2:11]2)=[CH:8][C:7](=[O:26])[CH2:6][CH2:5]1.[CH3:28][O:29][CH2:30][C:31](Cl)=[O:32]>>[OH:1][C@H:2]1[CH2:22][C@@:21]2([CH3:23])[C@@H:13]([CH2:14][CH2:15][C@:16]2([OH:24])[C:17](=[O:20])[CH2:18][O:19][C:31](=[O:32])[CH2:30][O:29][CH3:28])[C@H:12]2[C@H:3]1[C@:4]1([CH3:27])[C:9]([C@@H:10]([CH3:25])[CH2:11]2)=[CH:8][C:7](=[O:26])[CH2:6][CH2:5]1

Participants

Reactant 2

HCID 96623Methoxyacetyl chloride

HCID 1021476alpha-Methylhydrocortisone

Product 1

HCID 7050179511beta,17-Dihydroxy-21-methoxyacetoxy-6alpha-methyl-4-pregnene-3,20-dione

Procedure

1.5 g of 11β,17,21-trihydroxy-6α-methyl-4-pregnene-3,20-dione is reacted analogously to Example 1(a) with methoxyacetic acid chloride, worked up, and chromatographed, thus isolating 1.6 g of 11β,17-dihydroxy-21-methoxyacetoxy-6α-methyl-4-pregnene-3,20-dione.

Workup

customchromatographed

Sources & evidence

ORD record: ord-e65678ce00d24710ad0a1e0b2007dc3d
Source dataset: uspto-grants-1984_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04435390

Reaction notes

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