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

HRID 532779노트

반응식

HRID 532779 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 mixture was stirred at room temperature overnight and concentrated in vacuo. The 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 mixture was dried over Na2SO4 and concentrated in vacuo. 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 mixture was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customResidual HCl was removed
  7. customby evaporating from toluene

출처 및 근거

ORD 기록
ord-2537a0531c9e442a97104aa87eb1d4d4
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853199B2

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