Triethylamine → HCID 11004632, compound

HRID 1634513Notes

Reaction equation

HRID 1634513 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH2:12][CH:13]([CH2:19][CH3:20])[C:14]([O:16][CH2:17][CH3:18])=[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:34][C:35]([F:45])([F:44])[C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH2:41])=[CH:38][CH:37]=1>ClC(Cl)C.ClCCl>[CH2:19]([CH:13]([CH2:12][C:6]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([C:1](=[O:3])[NH:41][CH2:40][C:39]2[CH:38]=[CH:37][C:36]([C:35]([F:34])([F:44])[F:45])=[CH:43][CH:42]=2)[CH:5]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 768044-(Trifluoromethyl)benzylamineHCID 10891241HCID 10891241, compound

Product 1

HCID 11004632HCID 11004632, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 63651,1-DichloroethaneSolvent

Procedure

Ethyl 3-(3-carboxy-4-methoxyphenyl)-2-ethylpropanoate (5.00 g, 17.8 mmol) was dissolved in 80 ml of dehydrated dichloroethane, which was cooled to −10° C. to −15° C. Triethylamine (6.21 ml, 44.5 mmol) was added under stirring. Next, ethyl chlorocarbonate (1.86 ml, 19.5 mmol), dissolved in 10 ml of dehydrated dichloromethane was added dropwise. After stirring for 10 minutes at −10° C., 4-(trifluoromethyl)benzylamine (2.51 ml, 17.8 mmol), dissolved in 10 ml of dehydrated dichloromethane was added dropwise.

Workup

  1. temperaturewhich was cooled to −10° C. to −15° C
  2. additionwas added dropwise
  3. stirringAfter stirring for 10 minutes at −10° C.
  4. additionwas added dropwise

Sources & evidence

ORD record
ord-e05e2069cbc24546876caa06c0118f5b
Source dataset
uspto-grants-2003_01
Patent number
US06506797B1

Reaction notes

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