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

HRID 1823924노트

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HRID 1823924 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-abcf6e0a239345a1bae17a3dd71407b6
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07041687B2

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