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

HRID 1196821Notes

Reaction equation

HRID 1196821 reaction equation
[CH:1]([NH:3][C@H:4]([C:9]([OH:11])=O)[CH2:5][CH2:6][S:7][CH3:8])=[O:2].[F:12][C@:13]12[C@@H:33]([OH:34])[CH2:32][C@@:31]3([CH3:35])[C@@H:23]([CH2:24][C@H:25]([CH3:37])[C@:26]3([OH:36])[C:27](=[O:30])[CH2:28][SH:29])[C@@H:22]1[CH2:21][CH2:20][C:19]1[C@:14]2([CH3:39])[CH:15]=[CH:16][C:17](=[O:38])[CH:18]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[F:12][C@:13]12[C@@H:33]([OH:34])[CH2:32][C@@:31]3([CH3:35])[C@@H:23]([CH2:24][C@H:25]([CH3:37])[C@:26]3([OH:36])[C:27](=[O:30])[CH2:28][S:29][C:9](=[O:11])[CH:4]([NH:3][CH:1]=[O:2])[CH2:5][CH2:6][S:7][CH3:8])[C@@H:22]1[CH2:21][CH2:20][C:19]1[C@:14]2([CH3:39])[CH:15]=[CH:16][C:17](=[O:38])[CH:18]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 439750N-FormylmethionineHCID 1317173969-Fluoro-11beta,17-dihydroxy-16beta-methylpregna-1,4-diene-3,20-dione-21-thiol

Product 1

HCID 883953229-Fluoro-21-[2-(formylamino)-4-methylthio-1-oxobutylthio]-11beta,17-dihydroxy-16beta-methylpregna-1,4-diene-3,20-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

To a stirred solution of of N-formyl-L-methionine (7.8 gm) in dry ethyl acetate (120 ml) were added 9-fluoro-11β,17-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione-21-thiol (6.0 gm) in dry ethyl acetate (100 ml) and dicyclohexylcarbodiimide (18.2 gm) in dry ethyl acetate (100 ml) at room temperature. The reaction mixture was stirred at room temperature for for 4 hours.

Sources & evidence

ORD record
ord-a5283a231a044dfbb7bdc8b85df1d062
Source dataset
uspto-grants-1992_05
Patent number
US05116829

Reaction notes

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