Acetic Anhydride → HCID 13131731, compound

HRID 279828Notes

Reaction equation

[C:1]([O:9][C@:10]1([C@:31]2([CH3:32])[C@H:17]([C@H:18]3[C@H:28]([C@@H:29]([OH:33])[CH2:30]2)[C@:26]2([CH3:27])[C:21](=[CH:22][C:23](=[O:34])[CH:24]=[CH:25]2)[C@@H:20]([CH3:35])[CH2:19]3)[CH2:16][CH2:15]1)[C:11](=[O:14])[CH2:12][OH:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:36](OC(=O)C)(=[O:38])[CH3:37]>>[C:36]([O:13][CH2:12][C:11](=[O:14])[C@:10]1([O:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@:31]2([CH3:32])[C@H:17]([C@H:18]3[C@H:28]([C@@H:29]([OH:33])[CH2:30]2)[C@:26]2([CH3:27])[C:21](=[CH:22][C:23](=[O:34])[CH:24]=[CH:25]2)[C@@H:20]([CH3:35])[CH2:19]3)[CH2:16][CH2:15]1)(=[O:38])[CH3:37]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 13131723HCID 13131723, compound

Product 1

HCID 13131731HCID 13131731, compound

Procedure

1.9 g of 17-benzoyloxy-11β,21-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione is reacted, analogously to Example 2c, with acetic anhydride and worked up. The crude product is purified on 200 g of silica gel with a methylene chloride-acetone gradient (0-12% acetone), thus isolating 1.8 g of 21-acetoxy-17-benzoyloxy-11β-hydroxy-6α-methyl-1,4-pregnadiene-3,20-dione, mp 258° C.

Workup

customThe crude product is purified on 200 g of silica gel with a methylene chloride-acetone gradient (0-12% acetone)

Sources & evidence

ORD record: ord-1678e956d8254e4586940b920ddcc43c
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04587236

Reaction notes

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