Trifluoroacetic acid → N-(5,6,7,8-Tetrahydro-4H-thiazolo[4,5-d]azepin-2-yl)-acetamide

HRID 239159Notes

Reaction equation

HRID 239159 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:21][CH2:20][C:19]2[S:22][C:23]([NH:25][C:26](=[O:28])[CH3:27])=[N:24][C:18]=2[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)(Cl)Cl>[S:22]1[C:19]2[CH2:20][CH2:21][NH:15][CH2:16][CH2:17][C:18]=2[N:24]=[C:23]1[NH:25][C:26](=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866860352-Acetylamino-4,5,7,8-tetrahydro-thiazolo(4,5-d)azepine-6-carboxylic acid tert-butyl ester

Product 1

HCID 19985946N-(5,6,7,8-Tetrahydro-4H-thiazolo[4,5-d]azepin-2-yl)-acetamideYield 79.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

35 mL trifluoroacetic acid was added to 2.4 g 2-acetylamino-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepine-6-carboxylic acid tert-butyl ester in 80 mL chloroform. The reaction was stirred 3 h at RT and concentrated. The residue was dissolved in 75 mL chloroform and basified with 2.5 M potassiumcarbonate solution. The chloroform layer was separated and concentrated to give 1.3 g of the desired product. (M+H)+=212

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in 75 mL chloroform and basified with 2.5 M potassiumcarbonate solution
  3. customThe chloroform layer was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c1f2abfcfb954a499351fdb7eca5dc44
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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