Trifluoroacetic acid → HCID 22057735, compound

HRID 1828700Notes

Reaction equation

HRID 1828700 reaction equation
C([O:5][C:6](=[O:35])[CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][S:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:21]([C:31]([F:34])([F:33])[F:32])[CH:20]=2)=[CH:13][CH:12]=1)(C)(C)C.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:34][C:31]([F:32])([F:33])[C:21]1[CH:20]=[C:19]([S:18][CH2:17][C:14]2[CH:15]=[CH:16][C:11]([CH2:10][NH:9][CH2:8][CH2:7][C:6]([OH:35])=[O:5])=[CH:12][CH:13]=2)[CH:24]=[CH:23][C:22]=1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 69136002HCID 69136002, compound

Product 1

HCID 22057735HCID 22057735, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[4-(2-trifluoromethyl-biphenyl-4-ylsulfanylmethyl)-benzylamino]-propionic acid tert-butyl ester (24 mg, 0.0478 mmol, 1 eq.) in DCM (2 mL) is added triethylsilane (0.038 mL, 0.2392 mmol, 5 eq.) followed by TFA (2 mL). The mixture is stirred at room temperature for 2 h. After concentration, the crude product is purified by preparative RP LC-MS to give 3-[4-(2-Trifluoromethyl-biphenyl-4-ylsulfanylmethyl)-benzylamino]-propionic acid: 1H NMR (CD3OD, 400 MHz) δ7.66 (s, 1H), 7.60 (d, 1H), 7.55–7.38 (m, 7H), 7.28–7.21 (m, 3H), 4.33 (s, 2H), 4.18 (s, 2H), 3.26 (t, 2H), 2.72 (t, 2H); MS (ES+): (446.1, M+1)+.

Workup

  1. concentrationAfter concentration
  2. customthe crude product is purified by preparative RP LC-MS

Sources & evidence

ORD record
ord-d41d23f70f9d4f6eb118b8afe3b09189
Source dataset
uspto-grants-2006_06
Patent number
US07060697B2

Reaction notes

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