Trifluoroacetic acid → Trifluoroacetate

HRID 736675Notes

Reaction equation

HRID 736675 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([S:31][C:32]1[S:33][C:34]3[C:40]([Cl:41])=[CH:39][CH:38]=[CH:37][C:35]=3[N:36]=1)[N:6]2[CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:30])[C@@H:20]([NH:22]C(=O)OC(C)(C)C)[CH3:21])[CH2:15][CH2:14]1.[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43]>C(Cl)Cl>[NH2:22][C@@H:20]([CH3:21])[C:19]([N:16]1[CH2:15][CH2:14][CH:13]([CH2:12][CH2:11][N:6]2[C:5]([S:31][C:32]3[S:33][C:34]4[C:40]([Cl:41])=[CH:39][CH:38]=[CH:37][C:35]=4[N:36]=3)=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[NH2:1])[CH2:18][CH2:17]1)=[O:30].[F:45][C:44]([F:47])([F:46])[C:42]([O-:48])=[O:43]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57850166tert-Butyl {(1S)-2-[4-(2-{6-amino-8-[(7-chloro-1,3-benzothiazol-2-yl)thio]-9H-purin-9-yl}ethyl)piperidin-1-yl]-1-methyl-2-oxoethyl}carbamate

Product 2

HCID 84468TrifluoroacetateHCID 578503339-(2-{1-[(2S)-2-Aminopropanoyl]piperidin-4-yl}ethyl)-8-[(7-chloro-1,3-benzothiazol-2-yl)thio]-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc protected product from example 773 in DCM was added TFA and stirred at room temperature for 3 h. The solvent and excess TFA was evaporated under reduced pressure and the residual TFA was removed by co-evaporating with toluene to give title product as trifluoroacetate salt. 1H NMR δ (CD3OD), 8.35 (s, 1H), 7.84-7.82 (m, 1H), 7.50-7.40 (m, 2H), 4.40 (t, J=7.2 Hz, 2H), 4.00-3.90 (m, 1H), 1.80-1.70 (m, 4H), 1.41-1.37 (m, 4H), 1.32-1.30 (m, 3H), 1.20 (s, 3H); LC-MS [M+H]+ 517.1

Workup

  1. customThe solvent and excess TFA was evaporated under reduced pressure
  2. customthe residual TFA was removed by co-evaporating with toluene

Sources & evidence

ORD record
ord-3a9d8f7123d74d5da6cf426e2325b809
Source dataset
uspto-grants-2009_09
Patent number
US07595401B2

Reaction notes

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