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

HRID 1413966Notes

Reaction equation

HRID 1413966 reaction equation
[CH2:1]([C:8]1[CH:12]=[CH:11][NH:10][C:9]=1[CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:24]=1[NH:33][C@H:34]([C:38]([OH:40])=[O:39])[CH:35]([CH3:37])[CH3:36]>CCOCC>[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:24]=1[NH:33][C@H:34]([C:38]([OH:40])=[O:39])[CH:35]([CH3:37])[CH3:36].[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:24]=1[NH:33][CH:34]([CH:35]([CH3:37])[CH3:36])[C:38]([O:14][CH2:13][C:9]1[NH:10][CH:11]=[CH:12][C:8]=1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:39]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 156536L-Valine, N-[2-chloro-4-(trifluoromethyl)phenyl]-HCID 543430813-Benzyl-1-pyrrolylmethanol

Product 2

HCID 156536L-Valine, N-[2-chloro-4-(trifluoromethyl)phenyl]-HCID 202892863-Benzylpyrrolylmethyl 2-(2-chloro-4-trifluoromethylphenylamino)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 3-benzylpyrrolylmethyl alcohol (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 chromatography, eluting with 20% ether/hexane, gives the 3-benzylpyrrolylmethyl ester of N-(2-chloro-4-trifluoromethylphenyl)valine, [3-benzylpyrrolylmethyl 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-1155dafd247b4307ba46b67164b40bc9
Source dataset
uspto-grants-1981_02
Patent number
US04252724

Reaction notes

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