Trifluoroacetic acid → HCID 17984415, compound

HRID 1181112Notes

Reaction equation

HRID 1181112 reaction equation
C([O:5][C:6](=[O:39])[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:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:21][CH:22]=2)=[CH:11][C:10]=1[CH2:29][O:30][C:31](=[O:38])[NH:32][CH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:33]1([NH:32][C:31]([O:30][CH2:29][C:10]2[CH:11]=[C:12]([O:15][CH2:16][CH2:17][C:18]3[N:19]=[C:20]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[O:21][CH:22]=3)[CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]([OH:39])=[O:5])=[O:38])[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69229713HCID 69229713, compound

Product 1

HCID 17984415HCID 17984415, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 15 mL round bottom flask was charged with 3-{2-cyclopentylcarbamoyloxymethyl-4-[2-(2-phenyloxazol-4-yl)ethoxy]phenyl}propionic acid tert-butyl ester (0.097 g, 0.18 mmol), CH2Cl2 (1.2 mL), and then trifluoroacetic acid (1.2 mL). The solution was stirred at ambient temperature under a nitrogen atmosphere for 4 h and was concentrated. The residue was purified using radial chromatography (MeOH:CH2Cl2 2:98 to 10:90) to give a white solid (0.085 g, 93%). 1H NMR (400 MHz, CDCl3) δ 1.37 (br s, 2H), 1.63 (br s, 4H), 1.93-2.05 (m, 2H), 2.39 (s, 3H), 2.64 (br s, 2H), 2.91-3.18 (m, 4H), 3.99 (br s, 1H), 4.21 (s, 2H), 4.87 (br s, 1H), 5.10 (br s, 2H), 6.80 (s, 1H), 6.89 (s, 1H), 7.00-7.25 (br s, 1H), 7.36-7.52 (m, 3H), 7.95 (s, 2H). MS (ES) m/e 493 (M+1).

Workup

  1. concentrationwas concentrated
  2. customThe residue was purified

Sources & evidence

ORD record
ord-a7ca35379ad540e2a706818c70a2efe0
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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