Trifluoroacetic acid → Trifluoroacetic acid

HRID 2246581Notes

Reaction equation

HRID 2246581 reaction equation
[C:1]([NH:4][C@H:5]1[C@@H:10]([N:11]2[CH2:15][CH2:14][C@H:13]([NH:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]([F:30])([F:29])[F:28])[CH:25]=4)[N:20]=[CH:19][N:18]=3)[C:12]2=[O:31])[CH2:9][CH2:8][C@@H:7]([NH:32]C(=O)OC(C)(C)C)[CH2:6]1)(=[O:3])[CH3:2].[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43]>ClCCl>[NH2:32][C@H:7]1[CH2:6][C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[C@@H:10]([N:11]2[CH2:15][CH2:14][C@H:13]([NH:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]([F:29])([F:30])[F:28])[CH:25]=4)[N:20]=[CH:19][N:18]=3)[C:12]2=[O:31])[CH2:9][CH2:8]1.[C:42]([OH:44])([C:41]([F:46])([F:45])[F:40])=[O:43]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86618150HCID 86618150, compound

Product 2

HCID 6422Trifluoroacetic acidYield 86%HCID 24794656HCID 24794656, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirring solution of tert-butyl (1R,3R,4S)-3-acetamido-4-((S)-2-oxo-3-(6-(trifluoromethyl)quinazolin-4-ylamino)pyrrolidin-1-yl)cyclohexylcarbamate (1.65 g, 3 mmol) in dichloromethane (8 mL) was charged with trifluoroacetic acid (4 mL). The reaction was stirred for 1 h at room temperature and concentrated in vacuo. The residue was dissolved in a mixture of 1 mL of methanol and 5 mL of dichloromethane. The resulting solution was added dropwise to 80 mL of t-butylmethylether with stirring. The solid formed was collected with filtration and dried to give the title compound as its TFA salt (1.75 g, 86%). LC/MS found [M+H]+=451. 1H-NMR (400 MHz, CD3OD), δ ppm: 8.82 (1H, s), 8.77 (1H, s), 8.20-8.27 (1H, m), 7.95 (1H, d, J=8.65 Hz), 5.32 (1H, t, J=9.92 Hz), 4.36 (1H, t, J=4.07 Hz), 4.16-4.23 (1H, m), 3.87 (1H, t, J=9.16 Hz), 3.70-3.79 (1H, m), 3.39 (1H, s), 2.54-2.67 (1H, m), 2.32-2.45 (1H, m), 2.08-2.23 (2H, m), 1.88-2.04 (6H, m), 1.73-1.87 (1H, m).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in a mixture of 1 mL of methanol and 5 mL of dichloromethane
  3. additionThe resulting solution was added dropwise to 80 mL of t-butylmethylether
  4. stirringwith stirring
  5. customThe solid formed
  6. filtrationwas collected with filtration
  7. customdried

Sources & evidence

ORD record
ord-742d819b0b0d41608a26a5f1e463ed69
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

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