1,2-Dichloroethane → Methyl 2-{[4-(2-oxo-2-{[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]methyl}-benzoate

HRID 2111970Notes

Reaction equation

HRID 2111970 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)=[O:4].[F:23][C:24]([F:34])([F:33])[C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.C(Cl)CCl.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[O:18]=[C:16]([NH:30][CH2:29][C:28]1[CH:27]=[CH:26][C:25]([C:24]([F:23])([F:33])[F:34])=[CH:32][CH:31]=1)[CH2:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:7][C:6]2[CH:19]=[CH:20][CH:21]=[CH:22][C:5]=2[C:3]([O:2][CH3:1])=[O:4])=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 768044-(Trifluoromethyl)benzylamineHCID 68869545[(4-{[2-(Methoxycarbonyl)benzyl]oxy}phenyl)]acetic acid

Product 1

HCID 68869576Methyl 2-{[4-(2-oxo-2-{[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]methyl}-benzoateYield 95%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(4-{[2-(Methoxycarbonyl)benzyl]oxy}phenyl)acetic acid (50 mg, 0.167 mmol) was dissolved in DCM (2 ml), 4-(Trifluoromethyl)benzylamine (35 mg, 0.2 mmol) was added, then EDC (38 mg, 0.2 mmol) was added and then DMAP (24.4 mg, 0.2 mmol) was added. The mixture was stirred at room temperature overnight. 1% hydrochloric acid (1 ml) and water (1 ml) was added into the mixture. The two phases were separated using a Whatman Filter Tube. The obtained organic solution was evaporated in vacuum and the solid product (72 mg) was left, yield 95%.

Workup

  1. customThe two phases were separated
  2. filtrationFilter Tube
  3. customThe obtained organic solution was evaporated in vacuum
  4. waitthe solid product (72 mg) was left

Sources & evidence

ORD record
ord-e6383a481e4546ff8ca5b8c064b14289
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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