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

HRID 1181134Notes

Reaction equation

HRID 1181134 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:52])[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](=[O:40])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:29][CH:28]=2)=[CH:18][C:17]=1[CH2:41][O:42][C:43](=[O:51])[NH:44][CH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1)(C)(C)C>C(Cl)Cl>[C:33]([C:30]1[CH:29]=[CH:28][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:52])=[O:12])=[C:17]([CH2:41][O:42][C:43](=[O:51])[NH:44][CH:45]3[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)[CH:18]=2)=[CH:32][CH:31]=1)(=[O:40])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 589794473-{4-[3-(4-Benzoyl-phenoxy)-propoxy]-2-cyclohexylcarbamoyloxymethyl-phenyl}-propionic acid tert-butyl ester

Product 1

HCID 179844883-{4-[3-(4-Benzoyl-phenoxy)-propoxy]-2-cyclohexylcarbamoyloxymethyl-phenyl}-propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.031 mL, 0.4 mmol) was added to a solution of 3-{4-[3-(4-benzoyl-phenoxy)-propoxy]-2-cyclohexylcarbamoyloxymethyl-phenyl}-propionic acid tert-butyl ester (50 mg, 0.08 mmol) in CH2Cl2 (5 mL) at room temperature. The reaction mixture was stirred overnight and concentrated under vacuum to give the title compound. (39 mg, 88%). 1H-NMR (200 MHz, CDCl3): δ 7.83-7.72 (m, 4H), 7.57-7.43 (m, 3H), 7.12 (d, 1H, J=8.6), 6.98-82 (m, 4H), 5.10 (s, 2H), 4.82 (br s, 1H), 4.23 (t, 2H, J=5.9), 4.15 (t, 2H, J=5.9), 3.57-3.36 (m, 1H), 2.94 (m, 2H), 2.62 (m, 2H), 2.28 (qn, 2H, J=5.9), 1.98-1.02 (m, 10H).

Workup

  1. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f78c35e842494be89422c157c561b416
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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