Diisopropylethylamine → (2'-{[(3,5-Dichloro-benzyloxycarbonyl)-ethyl-amino]-methyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

HRID 1919980Notes

Reaction equation

HRID 1919980 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][NH:24][CH2:25][CH3:26])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.C(N(C(C)C)CC)(C)C.Cl[C:38]([O:40][CH2:41][C:42]1[CH:47]=[C:46]([Cl:48])[CH:45]=[C:44]([Cl:49])[CH:43]=1)=[O:39]>C(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:20])[F:22])=[CH:15][C:14]=2[CH2:23][N:24]([C:38]([O:40][CH2:41][C:42]2[CH:43]=[C:44]([Cl:49])[CH:45]=[C:46]([Cl:48])[CH:47]=2)=[O:39])[CH2:25][CH3:26])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 133055323,5-Dichlorobenzyl ChloroformateHCID 66603748(2'-Ethylaminomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

Product 1

HCID 66604037(2'-{[(3,5-Dichloro-benzyloxycarbonyl)-ethyl-amino]-methyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To (2′-ethylaminomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.101 g, 0.26 mmol) and diisopropylethylamine (0.23 mL, 1.32 mmol) in CH2Cl2 (1 mL) was added 3,5-dichlorobenzyl chloroformate (1.06 mmol) in CH2Cl2, and the reaction was stirred at room temperature for 5 minutes. The mixture was diluted with H2O and extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, decanted, and concentrated, and the residue was purified by silica gel chromatography to give the title compound.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customdecanted
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9283a7990f9245999645fc89ecc6b38d
Source dataset
uspto-grants-2012_05
Patent number
US08168678B2

Reaction notes

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