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

HRID 1196822Notes

Reaction equation

HRID 1196822 reaction equation
[CH:1]([NH:3][C@H:4]([C:9]([OH:11])=O)[CH2:5][CH2:6][S:7][CH3:8])=[O:2].ON1C2C=CC=CC=2N=N1.[F:22][C@:23]12[C@@H:43]([OH:44])[CH2:42][C@@:41]3([CH3:45])[C@@H:33]([CH2:34][C@H:35]([CH3:47])[C@:36]3([OH:46])[C:37](=[O:40])[CH2:38][SH:39])[C@@H:32]1[CH2:31][CH2:30][C:29]1[C@:24]2([CH3:49])[CH:25]=[CH:26][C:27](=[O:48])[CH:28]=1.C(N(CC)CC)C>C(OCC)(=O)C>[F:22][C@:23]12[C@@H:43]([OH:44])[CH2:42][C@@:41]3([CH3:45])[C@@H:33]([CH2:34][C@H:35]([CH3:47])[C@:36]3([OH:46])[C:37](=[O:40])[CH2:38][S:39][C:9](=[O:11])[CH:4]([NH:3][CH:1]=[O:2])[CH2:5][CH2:6][S:7][CH3:8])[C@@H:32]1[CH2:31][CH2:30][C:29]1[C@:24]2([CH3:49])[CH:25]=[CH:26][C:27](=[O:48])[CH:28]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 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-dioneYield 87.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent4×

Procedure

To a stirred solution of N-formyl-L-methionine (11.13 gm) in dry ethyl acetate (200 ml) were added 1-hydroxybenzotriazol (9.71 gm) in dry ethyl acetate (100 ml) and dicyclohexylcarbodiimido (16.43 gm) in dry ethyl acetate (100 ml) each at room temperature. The reaction mixture was stirred for 1.5 hours. To the stirred reaction mixture was added dropwise a solution of 9-fluoro-11β,17-dihydroxy-16β-methylpregna -1,4-diene-3,20-dione-21-thiol (12.95 gm) and triethylamine (35 ml) in dry ethyl acetate (600 ml) at 0° C. for 1 hour. The reaction mixture was stirred at room temperature for 4.5 hours. The title compound (15.68 gm) was prepared by purifying the resulting reaction mixture in the same manner as in Synthetic Example 1.

Workup

  1. customTo the stirred reaction mixture
  2. stirringThe reaction mixture was stirred at room temperature for 4.5 hours
  3. customby purifying
  4. customthe resulting reaction mixture in the same manner as in Synthetic Example 1

Sources & evidence

ORD record
ord-ac7e077cc1444e3cad3dba6b5e5826c1
Source dataset
uspto-grants-1992_05
Patent number
US05116829

Reaction notes

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