Triethylamine → Methyl 3-[4-methoxy-3-[N-[[4-(trifluoromethyl)phenyl]methyl]carbamoyl]phenyl]-2,2-dimethylpropanoate

HRID 1634526Notes

Reaction equation

HRID 1634526 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH2:12][C:13]([CH3:19])([CH3:18])[C:14]([O:16][CH3:17])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])([OH:3])=O.C(N(CC)CC)C.C(Cl)(=O)OCC.[F:33][C:34]([F:44])([F:43])[C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=1>ClCCl>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:6]([CH2:12][C:13]([CH3:19])([CH3:18])[C:14]([O:16][CH3:17])=[O:15])=[CH:5][C:4]=1[C:1](=[O:3])[NH:40][CH2:39][C:38]1[CH:37]=[CH:36][C:35]([C:34]([F:33])([F:43])[F:44])=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 768044-(Trifluoromethyl)benzylamineHCID 10923463Methyl 3-(3-carboxy-4-methoxyphenyl)-2,2-dimethylpropanoate

Product 1

HCID 18678023Methyl 3-[4-methoxy-3-[N-[[4-(trifluoromethyl)phenyl]methyl]carbamoyl]phenyl]-2,2-dimethylpropanoateYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using methyl 3-(3-carboxy-4-methoxyphenyl)-2,2-dimethylpropanoate (204 mg, 0.766 mmol), triethylamine (135 ml, 0.969 mmol), ethyl chlorocarbonate (82.0 ml, 0.843 mmol), 4-(trifluoromethyl)benzylamine (120 ml, 0.842 mmol) and 8 ml of dehydrated dichloromethane and conducting the procedure similar to Example 7, 309 mg (95%) of the title compound were obtained as a colorless oil.

Sources & evidence

ORD record
ord-4f9ab3d80b1342edb8834d43923204fc
Source dataset
uspto-grants-2003_01
Patent number
US06506797B1

Reaction notes

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