Trifluoroacetic acid → {N-[(1R)-1-Carbamoyl-3-methyl-butyl]-N-(4-chlorobenzenesulfonyl)amino}acetic acid

HRID 507304Notes

Reaction equation

HRID 507304 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:34])[CH2:14][N:15]([C@@H:26]([C:31](=[O:33])[NH2:32])[CH2:27][CH:28]([CH3:30])[CH3:29])[S:16]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])(C)(C)C>C(Cl)Cl>[C:31]([C@H:26]([N:15]([CH2:14][C:13]([OH:34])=[O:12])[S:16]([C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)(=[O:17])=[O:18])[CH2:27][CH:28]([CH3:30])[CH3:29])(=[O:33])[NH2:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59001051{N-[(1R)-1-Carbamoyl-3-methyl-butyl]-N-(4-chlorobenzenesulfonyl)amino}acetic acid tert-butyl ester

Product 1

HCID 59001083{N-[(1R)-1-Carbamoyl-3-methyl-butyl]-N-(4-chlorobenzenesulfonyl)amino}acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (15 mL) was added to a solution of {N-[(1R)-1-carbamoyl-3-methyl-butyl]-N-(4-chlorobenzenesulfonyl)amino}acetic acid tert-butyl ester (0.50 g, 1-2 mmol) in CH2Cl2 (15 mL). The reaction was stirred at rt for 4 h. The reaction was then concentrated to a white solid (0.40 g, 92%), which was used without further purification. MS (ESI), (M+H)+ 363.1; 1H NMR (DMSO-d6, 500 MHz) δ 7.90 (dd, 2H, J=2.0, 6.8), 7-65 (dd, 2H, J=2.0, 6.8), 7.60 (s, 1H), 7-06 (s, 1H), 4.32 (d, 1H, J=18), 4.12 (t, 1H, J=8.0), 4.02 (d, 1H, J=18), 1.55-1.65 (m, 1H), 1.35-1.45 (m, 2H), 0.78 (d, 3H, J=6.1), 0.73 (d, 3H, J=6.1).

Workup

  1. concentrationThe reaction was then concentrated to a white solid (0.40 g, 92%), which
  2. customwas used without further purification

Sources & evidence

ORD record
ord-4a22cc637a2d4941ae706310a1428790
Source dataset
uspto-grants-2010_08
Patent number
US07786122B2

Reaction notes

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