Trifluoroacetic acid → 3,3-Dimethyl-4-{2-[4-(methyl-phenyl-carbamoyloxy)-phenyl]-ethylcarbamoyl}-butyric acid

HRID 1831420Notes

Reaction equation

HRID 1831420 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:8][C:7](=[O:9])[O:6][C:4](=[O:5])[CH2:3]1.C(N(C(C)C)CC)(C)C.[NH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30](=[O:39])[N:31]([CH3:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:25][CH:24]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:10][C:2]([CH3:1])([CH2:3][C:4](=[O:5])[NH:20][CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][C:30](=[O:39])[N:31]([CH3:38])[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:27][CH:28]=1)[CH2:8][C:7]([OH:6])=[O:9]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 778133,3-Dimethylglutaric anhydrideHCID 81531DiisopropylethylamineHCID 69520583Methyl-phenyl-carbamic acid 4-(2-amino-ethyl)phenyl Ester

Product 1

HCID 695181973,3-Dimethyl-4-{2-[4-(methyl-phenyl-carbamoyloxy)-phenyl]-ethylcarbamoyl}-butyric acidYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3,3-dimethylglutaric anhydride (0.3 mmol), diisopropylethylamine (0.30 mmol) and N-methyl-N-phenyl-carbamic acid 4-(2-amino-ethyl)phenyl ester as its TFA salt (0.3 mmol) in CH2Cl2 (3 mL) was stirred 1 h at rt. The mixture was washed with water and brine, dried and evaporated to give the title compound in 95% yield as an oil.

Workup

  1. washThe mixture was washed with water and brine
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-af994777683340ee9dc8a6c97ed4ee7f
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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