N-Formylmethionine → 6,9-Difluoro-21-[2-(formylamino)-4-methylthio-1-oxobutylthio]-11alpha,17-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione

HRID 1196825Notes

Reaction equation

HRID 1196825 reaction equation
[F:1][CH:2]1[C:22]2[C@:17]([CH3:24])([CH:18]=[CH:19][C:20](=[O:23])[CH:21]=2)[C@:16]2([F:25])[C@H:4]([C@H:5]3[C@:13]([CH3:27])([CH2:14][C@@H:15]2[OH:26])[C@@:8]([OH:28])([C:9](=[O:12])[CH2:10][SH:11])[C@@H:7]([CH3:29])[CH2:6]3)[CH2:3]1.[CH:30]([NH:32][C@H:33]([C:38](O)=[O:39])[CH2:34][CH2:35][S:36][CH3:37])=[O:31]>>[F:1][CH:2]1[C:22]2[C@:17]([CH3:24])([CH:18]=[CH:19][C:20](=[O:23])[CH:21]=2)[C@:16]2([F:25])[C@H:4]([C@H:5]3[C@:13]([CH3:27])([CH2:14][C@H:15]2[OH:26])[C@@:8]([OH:28])([C:9](=[O:12])[CH2:10][S:11][C:38](=[O:39])[CH:33]([NH:32][CH:30]=[O:31])[CH2:34][CH2:35][S:36][CH3:37])[C@H:7]([CH3:29])[CH2:6]3)[CH2:3]1

Participants

3

Reactant 2

HCID 439750N-FormylmethionineHCID 1317173996,9-Difluoro-11beta,17-dihydroxy-16beta-methylpregna-1,4-diene-3,20-dione-21-thiol

Product 1

HCID 884942416,9-Difluoro-21-[2-(formylamino)-4-methylthio-1-oxobutylthio]-11alpha,17-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dioneYield 32.8%

Procedure

The title compound (0.027 gm) was prepared from 6,9-difluoro-11β,17-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione-21-thiol (0.06 gm) and (N-formyl-L-methionine (0.175 gm) in the same manner as in Synthetic Example 1.

Sources & evidence

ORD record
ord-81cc4f1dfaa84af6b6957e9be8bb3152
Source dataset
uspto-grants-1992_05
Patent number
US05116829

Reaction notes

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