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

HRID 1196826Notes

Reaction equation

HRID 1196826 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]([CH3:32])[C@:15]3([O:25][C:26](=[O:31])[CH2:27][CH2:28][CH2:29][CH3:30])[C:16](=[O:19])[CH2:17][SH:18])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:34])[CH:4]=[CH:5][C:6](=[O:33])[CH:7]=1.[CH:35]([NH:37][C@H:38]([C:43](O)=[O:44])[CH2:39][CH2:40][S:41][CH3:42])=[O:36]>>[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]([CH3:32])[C@:15]3([O:25][C:26](=[O:31])[CH2:27][CH2:28][CH2:29][CH3:30])[C:16](=[O:19])[CH2:17][S:18][C:43](=[O:44])[CH:38]([NH:37][CH:35]=[O:36])[CH2:39][CH2:40][S:41][CH3:42])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:34])[CH:4]=[CH:5][C:6](=[O:33])[CH:7]=1

Participants

3

Reactant 2

HCID 439750N-FormylmethionineHCID 1317174009-Fluoro-11-hydroxy-16beta-methyl-17-(1-oxopentyloxy)-pregna-1,4-diene-3,20-dione-21-thiol

Product 1

HCID 883953579-Fluoro-21-[2-(formylamino)-4-methylthio-1-oxobutylthio]-11beta-hydroxy-16beta-methyl-17-(1-oxopentyloxy)-pregna-1,4-diene-3,20-dioneYield 16.2%

Procedure

The title compound (1.03 gm) was prepared from 9-fluoro-11 -hydroxy-16β-methyl-17-(1-oxopentyloxy)-pregna-1,4-diene-3,20-dione-21-thiol (4.80 gm) and N-formyl-L-methionine (6.15 gm) in the same manner as in Synthetic Example 1.

Sources & evidence

ORD record
ord-650ac7d3b62c4ae7a701a013a1ba783b
Source dataset
uspto-grants-1992_05
Patent number
US05116829

Reaction notes

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