Trifluoroacetic acid → N-[(2S)-2-amino-3-(3,5-difluorophenyl)propyl]-L-alanyl-N1-isobutyl-L-valinamide

HRID 1062897Notes

Reaction equation

HRID 1062897 reaction equation
C(OC([NH:8][C@@H:9]([CH2:28][C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[C:31]([F:36])[CH:30]=1)[CH2:10][NH:11][C@H:12]([C:14]([NH:16][C@H:17]([C:21]([NH:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH3:13])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C@@H:9]([CH2:28][C:29]1[CH:30]=[C:31]([F:36])[CH:32]=[C:33]([F:35])[CH:34]=1)[CH2:10][NH:11][C@H:12]([C:14]([NH:16][C@H:17]([C:21]([NH:23][CH2:24][CH:25]([CH3:26])[CH3:27])=[O:22])[CH:18]([CH3:19])[CH3:20])=[O:15])[CH3:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10152485N-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propyl]-L-alanyl-N1-isobutyl-L-valinamide

Product 1

HCID 10126926N-[(2S)-2-amino-3-(3,5-difluorophenyl)propyl]-L-alanyl-N1-isobutyl-L-valinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propyl]-L-alanyl-N1-isobutyl-L-valinamide (377 mg, 0.735 mmol) is stirred with 1.5 mL of trifluoroacetic acid and 3 mL of dichloromethane for 25 min. It is then concentrated on a rotary evaporator and then neutralized with several mL of saturated aqueous sodium bicarbonate. The product is taken up in ethyl ether containing about 1% methanol, washed with several more mL of bicarbonate solution and with brine, and then dried over Na2SO4. Concentration afforded a quantitative yield of the title compound as a yellow solid. HRMS (ESI) calcd for C21H34F2N4O2+H1 413.2728, found 413.2730.

Workup

  1. concentrationIt is then concentrated on a rotary evaporator
  2. washwashed with several more mL of bicarbonate solution and with brine
  3. dry with materialdried over Na2SO4
  4. concentrationConcentration

Sources & evidence

ORD record
ord-97c1cd78ea3f4bf39f5e8cbece01dc09
Source dataset
uspto-grants-2005_11
Patent number
US06962934B2

Reaction notes

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