Trifluoroacetic acid → HCID 24951982, compound

HRID 1512023Notes

Reaction equation

HRID 1512023 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([S:35][C:36]1[C:44]([Br:45])=[CH:43][C:39]3[O:40][CH2:41][O:42][C:38]=3[CH:37]=1)[N:6]2[C:11]1[CH:34]=[CH:33][C:14]([CH2:15][C@@H:16]([C:25]([O:27][CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[O:26])[NH:17]C(OC(C)(C)C)=O)=[CH:13][CH:12]=1.C(O)(C(F)(F)F)=O.CO.C(Cl)Cl>C(Cl)Cl>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([S:35][C:36]1[C:44]([Br:45])=[CH:43][C:39]3[O:40][CH2:41][O:42][C:38]=3[CH:37]=1)[N:6]2[C:11]1[CH:12]=[CH:13][C:14]([CH2:15][C@@H:16]([C:25]([O:27][CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[O:26])[NH2:17])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21226129Dichloromethane methanolHCID 68696459HCID 68696459, compound

Product 1

HCID 24951982HCID 24951982, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of cyclopentyl 4-{6-amino-8-[(6-bromo-1,3-benzodioxol-5-yl)thio]-9H-purin-9-yl}-N-(tert-butoxycarbonyl)-L-phenylalaninate (44 mg, 0.063 mmol) in TFA (250 μl, 3.24 mmol) and DCM (1 ml) was stirred at room temp for 2 h. Chromatography (silica gel, 2-5% MeOH/DCM) afforded the title compound (20 mg) as a pale yellow solid. m/z 597 (M+H)+. 1H NMR (400 MHz, CHCl3-d) d: 8.28 (1H, s), 7.32-7.40 (4H, m), 7.03 (1H, s), 6.93 (1H, s), 6.00 (1H, s), 5.53 (2H, s), 5.20 (1H, m), 3.71 (1H, dd, J=7.8, 5.4 Hz), 3.13 (1H, dd, J=13.7, 5.4 Hz), 2.90 (1H, dd, J=13.7, 7.8 Hz), 1.86 (2H, m), 1.75-1.55 (10H, br m).

Sources & evidence

ORD record
ord-bf6f689092da4d6187fb195919a7d199
Source dataset
uspto-grants-2012_07
Patent number
US08217050B2

Reaction notes

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