Trifluoroacetic acid → 4-methyl-D-leucyl-N-[2-(1H-tetraazol-1-yl)-5-(trifluoromethyl)benzyl]-L-prolinamide
Reaction equation
C(O)(C(F)(F)F)=O.C(OC([NH:15][C@@H:16]([C:22]([N:24]1[CH2:47][CH2:46][CH2:45][C@H:25]1[C:26]([NH:28][CH2:29][C:30]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:31]=1[N:40]1[CH:44]=[N:43][N:42]=[N:41]1)=[O:27])=[O:23])[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=O)(C)(C)C>C(Cl)Cl>[CH3:19][C:18]([CH3:21])([CH3:20])[CH2:17][C@H:16]([C:22]([N:24]1[CH2:47][CH2:46][CH2:45][C@H:25]1[C:26]([NH:28][CH2:29][C:30]1[CH:35]=[C:34]([C:36]([F:37])([F:38])[F:39])[CH:33]=[CH:32][C:31]=1[N:40]1[CH:44]=[N:43][N:42]=[N:41]1)=[O:27])=[O:23])[NH2:15]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
TFA (1 mL) was added to a solution of N-(tert-butoxycarbonyl)-4-methyl-D-leucyl-N-[2-(1H-tetraazol-1-yl)-5-(trifluoromethyl)benzyl]-L-prolinamide (32 mg, 0.06 mmol) in dry CH2Cl2 (3 mL). The solution was stirred at room temperature for 30 min and was then concentrated in vacuo. The title compound was isolated by reverse phase HPLC as a white foam. 1H NMR (400 MHz, CD3OD)): δ 9.62 (s, 1H), 8.03 (s, 1H), 7.89 (dd, J=1.5, 8.2 Hz, 1H), 7.74 (d, J=8.3 Hz, 1H), 4.42 (d, J=15.6 Hz, 1H), 4.35 (d, J=15.6 Hz, 1H), 4.30 (dd, J=3.7, 8.6 Hz, 1H), 4.17 (apparent t, J=6.4 Hz, 1H), 3.83–3.78 (m, 1H), 3.62–3.56 (m, 1H), 2.25–2.18 (m, 1H), 2.15–1.85 (m, 4H), 1.64 (dd, J=6.8, 14.8 Hz, 1H), 1.01 (s, 9H). HRMS (ESI, M+H): 468.2324 (found); 468.2335 (calculated).
Workup
- concentrationwas then concentrated in vacuo
Sources & evidence
- ORD record
- ord-20228e5273dd45b98ce99fc94bc12e8f
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07144899B2
Reaction notes
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