Methylprednisolone → 21-Ethoxyacetoxy-11beta,17-dihydroxy-6alpha-methyl-1,4-pregnadiene-3,20-dione

HRID 1903058Notes

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

Participants

Reactant 2

HCID 6741Methylprednisolone

HCID 84189Ethoxyacetyl chloride

Product 1

HCID 1313558521-Ethoxyacetoxy-11beta,17-dihydroxy-6alpha-methyl-1,4-pregnadiene-3,20-dione

Procedure

As described in Example 2(a), 15.0 g of 11β,17,21-trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione is reacted with ethoxyacetic acid chloride, worked up, and purified, thus isolating 15.6 g of 21-ethoxyacetoxy-11β,17-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione, mp 229° C.

Workup

custompurified

Sources & evidence

ORD record: ord-5509af00ac2440539bb076358467db49
Source dataset: uspto-grants-1984_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04435390

Reaction notes

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