Triethylamine → L-Valine, N-[2-chloro-4-(trifluoromethyl)phenyl]-

HRID 224317Notes

Reaction equation

HRID 224317 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.[Cl:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[NH:35][C@H:36]([C:40]([OH:42])=[O:41])[CH:37]([CH3:39])[CH3:38]>CCOCC>[Cl:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[NH:35][C@H:36]([C:40]([OH:42])=[O:41])[CH:37]([CH3:39])[CH3:38].[Cl:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[NH:35][CH:36]([CH:37]([CH3:39])[CH3:38])[C:40]([O:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([F:1])=[C:3]([O:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:4]=1)=[O:41]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 156536L-Valine, N-[2-chloro-4-(trifluoromethyl)phenyl]-HCID 12874224(4-Fluoro-3-phenoxyphenyl)methanol

Product 2

HCID 156536L-Valine, N-[2-chloro-4-(trifluoromethyl)phenyl]-HCID 538801984-Fluoro-3-phenoxybenzyl 2-(2-chloro-4-trifluoromethylphenylamino)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 4-fluoro-3-phenoxybenzyl alcohol (0.22 g, 0.99 mmol) and triethylamine (0.14 g, 1.38 mmol) in ether (about 15 ml), under nitrogen, is added by syringe a solution of the acid chloride of N-(2-chloro-4-trifluoromethylphenyl) valine (1.5 mmol) in ether. The mixture is stirred for 30 minutes and then quenched with saturated aqueous sodium bicarbonate. The ether phase is washed with aqueous sodium bicarbonate, water and brine and filtered through silica. Evaporation of solvent, followed by thin layer chromatography using a circular chromatograph, eluting with 20% ether/hexane, gives the 4-fluoro-3-phenoxybenzyl ester of N-(2-chloro-4-trifluoromethylphenyl) valine, [4-fluoro-3-phenoxybenzyl 2-(2-chloro-4-trifluoromethylphenylamino)-3-methylbutanoate].

Workup

  1. customquenched with saturated aqueous sodium bicarbonate
  2. washThe ether phase is washed with aqueous sodium bicarbonate, water and brine
  3. filtrationfiltered through silica
  4. customEvaporation of solvent
  5. washeluting with 20% ether/hexane

Sources & evidence

ORD record
ord-f965e5be51014885a6719fcb448dfc2d
Source dataset
uspto-grants-1980_11
Patent number
US04231953

Reaction notes

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