Trifluoroacetic acid → 3-{4-[3-(Biphenyl-4-yloxy)-propoxy]-2-cyclohexylcarbamoyloxymethyl-phenyl}-propionic acid

HRID 1181132Notes

Reaction equation

HRID 1181132 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:50])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)=[CH:18][C:17]=1[CH2:39][O:40][C:41](=[O:49])[NH:42][CH:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1)(C)(C)C>C(Cl)Cl>[C:30]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:31]=[CH:32][C:27]([O:26][CH2:25][CH2:24][CH2:23][O:22][C:19]2[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][C:13]([OH:50])=[O:12])=[C:17]([CH2:39][O:40][C:41](=[O:49])[NH:42][CH:43]3[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]3)[CH:18]=2)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 589791993-{4-[3-(Biphenyl-4-yloxy)-propoxy]-2-cyclohexylcarbamoyloxymethyl-phenyl}-propionic acid tert-butyl ester

Product 1

HCID 179845663-{4-[3-(Biphenyl-4-yloxy)-propoxy]-2-cyclohexylcarbamoyloxymethyl-phenyl}-propionic acidYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.032 mL, 0.42 mmol) was added to a solution of 3-{4-[3-(biphenyl-4-yloxy)-propoxy]-2-cyclohexylcarbamoyloxymethyl-phenyl}-propionic acid tert-butyl ester (50 mg, 0.085 mmol) in CH2Cl2 (5 mL) at room temperature. The reaction mixture was stirred overnight and concentrated under vacuum to give the title compound (41 mg, 90%). 1H-NMR (200 MHz, CDCl3): δ 9.4 (br s, 1H), 7.58-7.49 (m, 4H), 7.42 (m, 2H), 7.32 (m, 1H), 7.13 (d, 1H, J=8.3), 7.00-6.93 (m, 3H), 6.84 (dd, 1H, J=7.8, 2.7), 5.11 (s, 2H), 4.76 (br s, 1H), 4.17 (m, 4H), 3.57-3.35 (m, 1H), 2.95 (t, 2H, J=7.8), 2.63 (t, 2H, J=7.8), 2.27 (qn, 2H, J=6.0), 1.99-1.05 (m, 10H).

Workup

  1. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4bd8bb2379664979aa98cd209b1ccead
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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