Trifluoroacetic acid → 3-{2-Cyclohexylcarbamoyloxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}propionic acid

HRID 1181118Notes

Reaction equation

HRID 1181118 reaction equation
C([O:5][C:6](=[O:41])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][O:31][C:32](=[O:40])[NH:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:34]1([NH:33][C:32]([O:31][CH2:30][C:10]2[CH:11]=[C:12]([O:15][CH2:16][CH2:17][C:18]3[N:19]=[C:20]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[O:21][C:22]=3[CH3:23])[CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]([OH:41])=[O:5])=[O:40])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 589795173-{2-Cyclohexylcarbamoyloxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}propionic acid tert-butyl ester

Product 1

HCID 101420763-{2-Cyclohexylcarbamoyloxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}propionic acidYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 25 mL round bottomed flask was charged with 3-{2-cyclohexylcarbamoyloxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}-propionic acid tert-butyl ester (0.080 g, 0.14 mmol) and CH2Cl2 (2 mL). Trifluoroacetic acid (2 mL) was added, and the solution was stirred at ambient temperature under a nitrogen atmosphere for 1.5 h. The solution was concentrated to give a white solid (0.068 g, 94%). 1H NMR (400 MHz, CDCl3) 1.08-1.18 (m 3H), 1.21-1.42 (m, 2H), 1.57 (br s, 1H), 1.66-1.70 (m, 2H), 1.90 (br s, 2H), 2.40 (s, 3H), 2.61 (t, J=7.7 Hz, 2H), 2.94 (t, J=7.8 Hz, 2H), 3.01 (t, J=6.4 Hz, 2H), 3.48 (br s, 1H), 4.22 (t, J=6.4 Hz, 2H), 4.74 (br s, 1H), 5.07 (s, 2H), 6.79-6.89 (m, 1H), 6.90 (s, 1H), 7.11 (d, J=8.3 Hz, 1H), 7.44-7.46 (m, 3H), 7.98 (dd, J=6.7, 2.8 Hz, 2H). MS (ES) m/e 507 (M+1).

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-186eecb5bd434b36919f734a27bc8771
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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