Benzylamine → (s)-2-(2-Benzylamino-5-trifluoromethyl-benzoylamino)-butyric acid tert-butyl ester

HRID 1091446ノート

反応式

HRID 1091446 の反応式
[C:1]([O:5][C:6](=[O:24])[C@@H:7]([NH:10][C:11](=[O:23])[C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1Cl)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC(C(F)(F)F)=CC=1C(O)=O.N[C@@H](CC)C(OC(C)(C)C)=O.[CH2:50]([NH2:57])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1.[Cl-].[NH4+].[Cu].[Cu]Br>[C:1]([O:5][C:6](=[O:24])[C@@H:7]([NH:10][C:11](=[O:23])[C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[NH:57][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2]

参加物

10

反応物 5

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 6881822-Chloro-5-(trifluoromethyl)benzoic acidHCID 7019938(2S)-2-amino butanic acid t-butyl esterHCID 66593952(s)-2-(2-Chloro-5-trifluoromethyl-benzoylamino)-butyric acid tert-butyl ester

生成物 1

HCID 57725377(s)-2-(2-Benzylamino-5-trifluoromethyl-benzoylamino)-butyric acid tert-butyl ester

試薬・触媒・溶媒 4

HCID 23978Copper触媒HCID 24593copper(I) bromide触媒HCID 84541-Methylpyrrolidine溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
160 °C

実験手順

To a solution of (S)-2-(2-chloro-5-trifluoromethyl-benzoylamino)-butyric acid tert-butyl ester (prepared from 2-chloro5-trifluoromethylbenzoic acid and (S)-2-aminobutyric acid, tert butyl ester in a procedure similar to that described in method F) (3 g) and benzylamine (1.1 ml) in N-methylpyrrolidine (40 ml) was added potassium carbonate (1.6 g), copper (30 mg) and copper (I) bromide (15 mg). The mixture was heated at 160° C. for 3 hours then cooled to room temp. and diluted with saturated ammonium chloride solution. The mixture was extracted with ethyl acetate and the organic solution dried (magnesium sulfate), filtered and concentrated. The residue was purified on silica gel, eluting with 15% ethyl acetate/hexane. The sub-titled product was obtained as a white solid (950 mg, 27%). 1H NMR (400 MHz, CDCl3) δ 1.04 (3H, t), 1.50 (9H, s), 2.86 (1H, m), 2.02 (1H, m), 4.50 (2H, d), 4.65 (1H, m), 6.69 (2H, m), 7.21-7.70 (7H, m), 8.42 (1H, m) ppm; MS ES (−) 435.32 (M−H).

後処理

  1. temperaturethen cooled to room temp.
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe organic solution dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel
  7. washeluting with 15% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-cd13b8842f9346ad826b7085cca4aab8
出典データセット
uspto-grants-2012_03
特許番号
US08129381B2

反応ノート

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