Trifluoroacetic acid → HCID 54029454, compound

HRID 2396089Notes

Reaction equation

HRID 2396089 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:47])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[CH2:16][C@@H:17]([NH:39]C(OC(C)(C)C)=O)[CH2:18][S:19]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(C(O)=O)(F)(F)F.C([SiH](CC)CC)C>C(Cl)Cl>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:47])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[CH2:16][C@@H:17]([NH2:39])[CH2:18][SH:19]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 53734933HCID 53734933, compound

Product 1

HCID 54029454HCID 54029454, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[2(R)-t-butoxycarbonylamino-3-triphenylmethylmercapto-propyl]-L-proline-2,3-dimethylphenyl amide (0.124 g, 0.19 mmol) was dissolved in CH2Cl2 (3 mL) and CF3CO2H (1 mL) at ambient temperature, treated with triethylsilane (0.121 mL, 0.76 mmol) and stirred for 2 h. Thereaction mixture was concentrated, triturated with 0.1% aq TFA soln, the solid precipitate filtered off, and the filtrate lyophilized to provide the title compound. 1H NMR (CD3OD) δ 7.10 (s, 3H), 3.55-3.68 (m, 1H), 3.32-3.45 (m, 2H), 2.75-3.19 (m, 5H), 2.5-2.65 (m, 1H),2.31 (s, 3H), 2.15 (s, 3H), 1.9-2.15 (m, 3H).

Workup

  1. concentrationThereaction mixture was concentrated
  2. customtriturated with 0.1% aq TFA soln
  3. filtrationthe solid precipitate filtered off

Sources & evidence

ORD record
ord-a15ccb0a90b44261ac69ffdb96c40f5a
Source dataset
uspto-grants-1996_02
Patent number
US05491164

Reaction notes

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