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Potassium Carbonate → N-(Diphenylmethylene) (3,4,5-trifluoro)-D,L-Phenylalanine ethyl ester

HRID 1365892
Notes
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Reaction equation

HRID 1365892 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].[F:21][C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([F:31])[C:29]=1[F:30])[CH2:25]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([CH2:25][C:24]1[CH:23]=[C:22]([F:21])[C:29]([F:30])=[C:28]([F:31])[CH:27]=1)[N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 27770623,4,5-Trifluorobenzyl bromide

Product 1

HCID 58584141N-(Diphenylmethylene) (3,4,5-trifluoro)-D,L-Phenylalanine ethyl esterYield 72.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of N-(Diphenylmethylene)glycine ethyl ester (1.10 g, 4.1 mmol) and 3,4,5-trifluorobenzylbromide (0.91 g, 4.0 mmol) in dimethylformamide (10 mL) was treated with anhydrous potassium carbonate (2.83 g, 20.5 mmol) and stirred for 18 hrs at 25° C. The mixture was filtered and the filtrate was evaporated to dryness to give crude product. It was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1) to give title compound (1.2 g).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. customto give crude product
  4. customIt was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-05b40dc57839432c85bea424e6b6107b
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07893020B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes