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

HRID 1196824Notes

Reaction equation

HRID 1196824 reaction equation
[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][C@@H:14]([CH3:26])[C@:15]3([OH:25])[C:16](=[O:19])[CH2:17][SH:18])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:28])[CH:4]=[CH:5][C:6](=[O:27])[CH:7]=1.[CH:29]([NH:31][C@H:32]([C:37](O)=[O:38])[CH2:33][CH2:34][S:35][CH3:36])=[O:30]>>[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][C@@H:14]([CH3:26])[C@:15]3([OH:25])[C:16](=[O:19])[CH2:17][S:18][C:37](=[O:38])[CH:32]([NH:31][CH:29]=[O:30])[CH2:33][CH2:34][S:35][CH3:36])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:28])[CH:4]=[CH:5][C:6](=[O:27])[CH:7]=1

Participants

3

Reactant 2

HCID 439750N-FormylmethionineHCID 1317173989-Fluoro-11beta,17-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione-21-thiol

Product 1

HCID 883953439-Fluoro-21-[2-(formylamino)-4-methylthio-1-oxobutylthio]-11beta,17-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dioneYield 24.5%

Procedure

The title compound (0.34 gm) was prepared from 9-fluoro-11β,17-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione-21-thiol (1.00 gm) and N-formyl-L-methionine (1.30 gm) in the same manner as in Synthetic Example 1.

Sources & evidence

ORD record
ord-124ee4a3da944810b6f87552decb3d52
Source dataset
uspto-grants-1992_05
Patent number
US05116829

Reaction notes

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