Trifluoroacetic acid → L-alanyl-L-valinamide

HRID 1062906Notes

Reaction equation

HRID 1062906 reaction equation
C(OC([NH:8][C@H:9]([C:11]([NH:13][C@H:14]([C:18]([NH2:20])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[CH3:10])=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:8][C@H:9]([C:11]([NH:13][C@H:14]([C:18]([NH2:20])=[O:19])[CH:15]([CH3:16])[CH3:17])=[O:12])[CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86589158N-(tert-butoxycarbonyl)-L-alanyl-L-valinamide

Product 1

HCID 7019981L-alanyl-L-valinamideYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(tert-butoxycarbonyl)-L-alanyl-L-valinamide (0.5 g, 1.74 mmol) is stirred with 3 mL of TFA in 6 mL of dichloromethane for 1 h. It is then concentrated, neutralized with 3.5 mL of 1N NaHCO3 and 3.5 mL of 1N Na2CO3, and extracted into 60 mL of ethyl ether containing several mL of methanol. The aqueous phase is extracted with 100 mL of dichloromethane and 10 mL of methanol. The aqueous layer is evaporated and the solids are extracted with methanol. This is concentrated to 180 mg (0.96 mmol, 55%) of an 85:15 mixture of the title compound and a minor diastereomer. The combined organic phases are concentrated to afford 74 mg (0.4 mmol, 23%) of the title compound as a white solid. HRMS (ESI) calcd for C8H17N3O2+H1 188.1399, found 188.1408.

Workup

  1. concentrationIt is then concentrated
  2. extractionextracted into 60 mL of ethyl ether containing several mL of methanol
  3. extractionThe aqueous phase is extracted with 100 mL of dichloromethane and 10 mL of methanol
  4. customThe aqueous layer is evaporated
  5. extractionthe solids are extracted with methanol
  6. concentrationThis is concentrated to 180 mg (0.96 mmol, 55%) of an 85:15 mixture of the title compound
  7. concentrationThe combined organic phases are concentrated

Sources & evidence

ORD record
ord-f203da0ac31841f6b35ae11f0198a72c
Source dataset
uspto-grants-2005_11
Patent number
US06962934B2

Reaction notes

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