Trifluoroacetic acid → Trifluoroacetic acid

HRID 1677595Notes

Reaction equation

HRID 1677595 reaction equation
[CH2:1]([C:8]([NH:38]C(=O)OC(C)(C)C)([CH2:36][OH:37])[CH2:9][NH:10][CH2:11][C:12]1[CH:17]=[C:16]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])[CH:15]=[C:14]([C:24]([NH:26][C@@H:27]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH3:28])=[O:25])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:46]([OH:52])([C:48]([F:51])([F:50])[F:49])=[O:47]>C(Cl)(Cl)Cl>[NH2:38][C:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH2:36][OH:37])[CH2:9][NH:10][CH2:11][C:12]1[CH:13]=[C:14]([CH:15]=[C:16]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:20])=[O:21])[CH:17]=1)[C:24]([NH:26][C@@H:27]([C:29]1[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=1)[CH3:28])=[O:25].[C:46]([OH:52])([C:48]([F:51])([F:50])[F:49])=[O:47]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67374250HCID 67374250, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 59553965HCID 59553965, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Treatment of Boc derivative from step B with 50% TFA in CHCl3 for 30 min, followed by concentration under a stream of nitrogen, and purification by preparative HPLC (5% to 95% CH3CN in water containing 0.1% TFA, C18 PRO YMC 20×150 mm) afforded 3-{[(2-amino-2-benzyl-3-hydroxypropyl)amino]methyl}-N-[(1R)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]benzamide as a bis TFA salt. 1H NMR (400 MHz, d4-MeOH) δ 8.85 (d, J=7.9 Hz, 1H), 7.84 (s, 2H), 7.67 (s, 1H), 7.46-7.38 (m, 2H), 7.36-7.25 (m, 3H), 7.25-7.18 (m, 2H), 7.10-7.00 (m, 2H), 5.40-5.18 (m, 1H), 4.12-4.00 (m, 2H), 3.66 (A of AB, d, J=11.0 Hz, 1H), 3.61 (B of AB, d, J=11.0 Hz, 1H), 3.35 (s, 3H), 3.06-2.88 (m, 2H), 2.95 (s, 3H), 1.58 (d, J=7.1 Hz, 3H).

Workup

  1. concentrationfollowed by concentration under a stream of nitrogen, and purification by preparative HPLC (5% to 95% CH3CN in water containing 0.1% TFA

Sources & evidence

ORD record
ord-c954a03d3ab245e8ad0109f1c68db7e9
Source dataset
uspto-grants-2011_08
Patent number
US08008315B2

Reaction notes

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