Water → 4-tert-Butoxycarbonylamino-2-(3,4-dichlorophenyl)-butyric acid

HRID 1823924ノート

反応式

HRID 1823924 の反応式
C[O:2][C:3](=[O:23])[CH:4]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].O.[OH-].[Li+]>C1COCC1>[C:11]([O:10][C:8]([NH:7][CH2:6][CH2:5][CH:4]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[C:3]([OH:23])=[O:2])=[O:9])([CH3:14])([CH3:12])[CH3:13]

参加物

5

反応物 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 235709514-Tert-butoxycarbonylamino-2-(3,4-dichlorophenyl)-butyric acid methyl ester

生成物 1

HCID 221479534-tert-Butoxycarbonylamino-2-(3,4-dichlorophenyl)-butyric acid収率 98%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-tert-butoxycarbonylamino-2-(3,4-dichlorophenyl)-butyric acid methyl ester (12.3 g, 34 mmol) in THF (80 mL)/water (20 mL) was added lithium hydroxide (1.63 g, 68 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated and the residue diluted with water. After extraction with EtOAc, the aqueous phase was acidified to pH 5 by the addition of 2M aqueous hydrochloric acid solution. The aqueous phase was extracted with EtOAc and the extracts dried over magnesium sulfate. Concentration gave the title compound as a pale brown foam (11.54 g, 98%); 1H NMR (400 MHz, DMSO) δ 1.35 (9H, s), 1.74–1.81 (1H, m), 2.03–2.10 (1H, m), 2.81 (2H, m), 3.61 (1H, t), 6.86 (1H, m), 7.28 (1H, dd), 7.54 (1H, dd), 7.59 (1H, d), 12.60 (1H, brs); MS (ES−) m/e=346.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue diluted with water
  3. extractionAfter extraction with EtOAc
  4. additionthe aqueous phase was acidified to pH 5 by the addition of 2M aqueous hydrochloric acid solution
  5. extractionThe aqueous phase was extracted with EtOAc
  6. dry with materialthe extracts dried over magnesium sulfate
  7. concentrationConcentration

出典と根拠

ORDレコード
ord-abcf6e0a239345a1bae17a3dd71407b6
出典データセット
uspto-grants-2006_05
特許番号
US07041687B2

反応ノート

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