Acetyl chloride → rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-1'-carboxylic acid (1-acetyl-piperidin-4-ylethyl)-amide

HRID 2065425Notes

Reaction equation

HRID 2065425 reaction equation
F[C:2](F)(F)[C:3](O)=[O:4].[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH:16][C:17]([N:19]2[CH2:23][CH:22]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:21]3([C:36]4[C:31](=[CH:32][C:33]([Cl:37])=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:38])[CH:20]2[C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[C:40]=2[F:46])=[O:18])[CH2:10][CH2:9]1.C(N(CC)CC)C.C(Cl)(=O)C>O1CCCC1>[C:3]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH:16][C:17]([N:19]2[CH2:23][CH:22]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:21]3([C:36]4[C:31](=[CH:32][C:33]([Cl:37])=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:38])[CH:20]2[C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[C:40]=2[F:46])=[O:18])[CH2:10][CH2:9]1)(=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 76021608HCID 76021608, compound

Product 1

HCID 76021611rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-1'-carboxylic acid (1-acetyl-piperidin-4-ylethyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in Example 26, rac-(2′S,3′S,4′S)-6-chloro-2′-(3-chloro-2-fluoro-phenyl)-4′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-1′-carboxylic acid (piperidin-4-ylethyl)-amide trifluoroacetic acid prepared in Example 51 (30 mg, 0.04 mmol) was reacted with triethylamine and acetyl chloride (3.8 mg, 0.05 mmol) in tetrahydrofuran to give rac-(2′S,3′S,4′S)-6-chloro-2′-(3-chloro-2-fluoro-phenyl)-4′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-1′-carboxylic acid (1-acetyl-piperidin-4-ylethyl)-amide as a white solid (Yield, 23 mg, 86%).

Workup

  1. customto give

Sources & evidence

ORD record
ord-8447d40c588747389aa46b2f2b37887b
Source dataset
uspto-grants-2012_10
Patent number
US08288431B2

Reaction notes

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