Dichloromethane → N-[(2S)-2-amino-3-phenylpropyl]-L-alanyl-N1-isobutyl-L-valinamide

HRID 1062893Notes

Reaction equation

HRID 1062893 reaction equation
C(OC([NH:8][C@@H:9]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][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>C(O)C>[NH2:8][C@@H:9]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][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

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 69734334N-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl]-L-alanyl-N1-isobutyl-L-valinamide

Product 1

HCID 69735335N-[(2S)-2-amino-3-phenylpropyl]-L-alanyl-N1-isobutyl-L-valinamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl]-L-alanyl-N1-isobutyl-L-valinamide (84 mg, 0.176 mmol) is stirred with 1 mL of trifluoroacetic acid and 3 mL of dichloromethane for 30 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 70 mL of ethyl ether, washed with several more mL of bicarbonate solution, and then dried over anhydrous sodium sulfate. Concentration from ethyl ether, and then from absolute ethanol, afforded 75 mg of a slightly yellow oil, whose NMR spectrum was consistent with the title compound, along with a small amount of residual ethanol. NMR (CDCl3) δ 7.96 (d, J=9 Hz, 1H), 7.3-7.17 (m, 5H), 6.88 (br t, 1H), 4.13 (m, 1H), 3.27 (m, 1H), 3.13 (m, 1H), 3.05 (m, 1H), 2.94 (m, 1H), 3.83 (m, 2H), 2.7 (dd, 1H), 2.57 (dd, 1H), 2.08 (m, 1H), 1.72 (m, 1H), 1.31 (d, J=7 Hz, 3H), 0.93-0.86 (overlapping d, 12H).

Workup

  1. concentrationIt is then concentrated on a rotary evaporator
  2. washwashed with several more mL of bicarbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationConcentration from ethyl ether
  5. customfrom absolute ethanol, afforded 75 mg of a slightly yellow oil, whose NMR spectrum

Sources & evidence

ORD record
ord-0a6de3c3574041d6b35cf901dc577e8a
Source dataset
uspto-grants-2005_11
Patent number
US06962934B2

Reaction notes

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