Trifluoroacetic acid → HCID 24951627, compound

HRID 1512022Notes

Reaction equation

HRID 1512022 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([S:29][C:30]1[C:38]([I:39])=[CH:37][C:33]3[O:34][CH2:35][O:36][C:32]=3[CH:31]=1)[N:6]2[CH2:11][C@@H:12]([C:21]([O:23][CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:22])[NH:13]C(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>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:29][C:30]1[C:38]([I:39])=[CH:37][C:33]3[O:34][CH2:35][O:36][C:32]=3[CH:31]=1)[N:6]2[CH2:11][C@@H:12]([C:21]([O:23][CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28]1)=[O:22])[NH2:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68696064HCID 68696064, compound

Product 1

HCID 24951627HCID 24951627, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of cyclopentyl 3-{6-amino-8-[(6-iodo-1,3-benzodioxol-5-yl)thio]-9H-purin-9-yl}-N-(tert-butoxycarbonyl)-L-alaninate (21 mg, 0.027 mmol) in TFA (250 μl, 3.24 mmol) and DCM (1 ml) was stirred at room temp for 2 h. LC-MS analysis showed complete formation of the product. The solvent was evaporated and the residue purified on SCX (0.5 g) to afford the title compound (12 mg) as a pale yellow solid. m/z 569 [M+H]+. 1H NMR (400 MHz, CHCl3-d) d: 8.31 (1H, s), 7.23 (1H, s), 6.93 (1H, s), 5.97 (2H, s), 5.61 (2H, br. s), 5.13 (1H, m), 4.50 (1H, dd, J=14.2, 5.9 Hz), 4.33 (1H, dd, J=113.9, 8.6 Hz), 3.98 (1H, dd, J=8.8, 5.9 Hz), 1.8-1.54 (10H, br m).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified on SCX (0.5 g)

Sources & evidence

ORD record
ord-3c63c0358a3c45c3b08fbea4d41197bf
Source dataset
uspto-grants-2012_07
Patent number
US08217050B2

Reaction notes

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