Acetyl chloride → 2-Acetylamino-4,5,7,8-tetrahydro-thiazolo(4,5-d)azepine-6-carboxylic acid tert-butyl ester

HRID 400430Notes

Reaction equation

HRID 400430 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([O:9][C:10]([N:12]1[CH2:18][CH2:17][C:16]2[S:19][C:20]([NH2:22])=[N:21][C:15]=2[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>N1C=CC=CC=1.ClCCl.O>[C:5]([O:9][C:10]([N:12]1[CH2:18][CH2:17][C:16]2[S:19][C:20]([NH:22][C:1](=[O:3])[CH3:2])=[N:21][C:15]=2[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 2

HCID 6367Acetyl chlorideHCID 84712457Tert-butyl 2-amino-4,5,7,8-tetrahydrothiazolo[5,4-d]azepine-6-carboxylate

Product 1

HCID 866860352-Acetylamino-4,5,7,8-tetrahydro-thiazolo(4,5-d)azepine-6-carboxylic acid tert-butyl esterYield 35.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

95 mg acetyl chloride was added to 312 mg 2-Amino-4,5,7,8-tetrahydro-thiazolo (4,5-d) azepine-6-carboxylic acid tert-butyl ester in 5 mL pyridine at 15° C. The reaction was stirred 3 h at RT. The reaction was diluted with dichlormethane and 1 mL water was added. The solution was filtered over 40 mL Alox and 100 mL Extrelut and evaporated to give 127 mg desired product. (M+H)+: 312

Workup

  1. additionwas added
  2. filtrationThe solution was filtered over 40 mL Alox and 100 mL Extrelut
  3. customevaporated

Sources & evidence

ORD record
ord-f26250d0153d457a99c51d7d3b736e55
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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