Lithium hydroxide, monohydrate → 4-(Tert-butoxycarbonylamino)-2-(4-chlorophenyl)-4-methylpentanoic acid

HRID 625038노트

반응식

HRID 625038 반응식
[OH2:1].[OH-].[Li+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:15](=[O:16])[N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:13]([CH3:25])([CH3:24])[CH2:12]2)=[CH:7][CH:6]=1>C1COCC1.CO.O>[C:20]([O:19][C:17]([NH:14][C:13]([CH3:25])([CH3:24])[CH2:12][CH:11]([C:8]1[CH:9]=[CH:10][C:5]([Cl:4])=[CH:6][CH:7]=1)[C:15]([OH:1])=[O:16])=[O:18])([CH3:23])([CH3:22])[CH3:21]

참가 물질

4

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 66617851Tert-butyl 4-(4-chlorophenyl)-2,2-dimethyl-5-oxopyrrolidine-1-carboxylate

생성물 1

HCID 666178284-(Tert-butoxycarbonylamino)-2-(4-chlorophenyl)-4-methylpentanoic acid수율 63.2%

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

Lithium hydroxide hydrate (6.44 ml, 232 mmol) was added to a stirred solution of tert-butyl 4-(4-chlorophenyl)-2,2-dimethyl-5-oxopyrrolidine-1-carboxylate (7.5 g, 23.2 mmol) in THF/MeOH/H2O (30 mL/30 mL/30 mL) at room temperature. The reaction mixture was stirred overnight and then concentrated in vacuo. The reaction mixture was taken up into water (200 mL), washed with EtOAc (100 mL), acidified with concentrated HCl and extracted into EtOAc (2×200 mL). The product was dried over Na2SO4 and concentrated in vacuo. The residual HCl was removed by evaporating from toluene to give 4-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)-4-methylpentanoic acid (5.0 g, 63.2% yield) as a white solid. LCMS (APCI+) [M-Boc+H]+ 242.0; Rt: 2.8 min.

후처리

  1. concentrationconcentrated in vacuo
  2. washwashed with EtOAc (100 mL)
  3. extractionextracted into EtOAc (2×200 mL)
  4. dry with materialThe product was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residual HCl was removed
  7. customby evaporating from toluene

출처 및 근거

ORD 기록
ord-faaffd049fd344ee85e11482451cf17e
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303040B2

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