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

HRID 224317ノート

反応式

HRID 224317 の反応式
[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]

参加物

6

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-f965e5be51014885a6719fcb448dfc2d
出典データセット
uspto-grants-1980_11
特許番号
US04231953

反応ノート

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