Acetyl chloride → HCID 86584860, compound

HRID 1006861Notes

Reaction equation

HRID 1006861 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([SH:13])[CH2:10][C@H:9]1[CH2:14][N:15]([C:25](=[O:27])[CH3:26])[CH2:16][C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[F:24])=[O:7])[CH2:2][CH2:3][CH3:4].[C:28](Cl)(=[O:30])[CH3:29]>N1C=CC=CC=1.C(Cl)Cl>[CH2:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][C:28](=[O:30])[CH3:29])[CH2:10][C@H:9]1[CH2:14][N:15]([C:25](=[O:27])[CH3:26])[CH2:16][C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[F:24])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 86584861HCID 86584861, compound

Product 1

HCID 86584860HCID 86584860, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

130 mg (0.325 mmol) [2S,4R]-2-{[acetyl-(2,5-difluoro-benzyl)-amino]-methyl}-4-mercapto-pyrrolidine-1-carboxylic acid butyl ester in 3 ml pyridine were treated with 120 μl (1.68 mmol, 5.1 eq) acetyl chloride at 0° C. The resulting suspension was diluted with 8 ml CH2Cl2, and the mixture was stirred at RT over night, concentrated in vacuo and the oil was redissolved in EtOAc/1M HCl. The inorganic phase was extracted with CH2Cl2 and the organic phases were washed with 1M HCl and brine, dried over Na2SO4. The crude product was purified by flash column chromatography with EtOAc/hexane 1:1 as eluent yielding 118.2 mg (82%) [2S,4R]-2-{[acetyl-(2,5-difluoro-benzyl)-amino]-methyl}-4-acetylsulfanyl-pyrrolidine-1-carboxylic acid butyl ester as light yellow oil, MS: 443 (MHf).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionthe oil was redissolved in EtOAc/1M HCl
  3. extractionThe inorganic phase was extracted with CH2Cl2
  4. washthe organic phases were washed with 1M HCl and brine
  5. dry with materialdried over Na2SO4
  6. customThe crude product was purified by flash column chromatography with EtOAc/hexane 1:1 as eluent

Sources & evidence

ORD record
ord-d6f15da1293f4083bad94a6f876b261d
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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