N-Formylmethionine → 9-Fluoro-21-[2-(formylamino)-4-methylthio-1-oxobutylthio]-11beta-hydroxy-16beta-methyl-17-(1-oxopropyloxy)-pregna-1,4-diene-3,20-dione

HRID 1196828Notes

Reaction equation

HRID 1196828 reaction equation
[F:1][C@:2]12[CH:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][C@H:14]([CH3:30])[C@:15]3([O:25][C:26](=[O:29])[CH2:27][CH3:28])[C:16](=[O:19])[CH2:17][SH:18])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:32])[CH:4]=[CH:5][C:6](=[O:31])[CH:7]=1.[CH:33]([NH:35][C@H:36]([C:41](O)=[O:42])[CH2:37][CH2:38][S:39][CH3:40])=[O:34]>>[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]([CH3:30])[C@:15]3([O:25][C:26](=[O:29])[CH2:27][CH3:28])[C:16](=[O:19])[CH2:17][S:18][C:41](=[O:42])[CH:36]([NH:35][CH:33]=[O:34])[CH2:37][CH2:38][S:39][CH3:40])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:32])[CH:4]=[CH:5][C:6](=[O:31])[CH:7]=1

Participants

3

Reactant 2

HCID 439750N-FormylmethionineHCID 1317174019-Fluoro-11 hydroxy-16beta-methyl-17-(1-oxopropyloxy)-pregna-1,4-diene-3,20-dione-21-thiol

Product 1

HCID 884939619-Fluoro-21-[2-(formylamino)-4-methylthio-1-oxobutylthio]-11beta-hydroxy-16beta-methyl-17-(1-oxopropyloxy)-pregna-1,4-diene-3,20-dioneYield 43.8%

Procedure

The title compound (0.47 gm) was prepared from 9-fluoro-11 hydroxy-16β-methyl-17-(1-oxopropyloxy)-pregna-1,4-diene-3,20-dione-21-thiol (0.80 gm) and N-formyl-L-methionine (0.99 gm) in the same manner as in Synthetic Example 1.

Sources & evidence

ORD record
ord-757afafb28134c37ba2099f58ecb7455
Source dataset
uspto-grants-1992_05
Patent number
US05116829

Reaction notes

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