Water → tert-butyl 4-[(2R)-3-benzyloxycarbonylamino-2-hydroxy-propyl]piperazine-1-carboxylate

HRID 2364707노트

반응식

HRID 2364707 반응식
[NH2:1][CH2:2][C@@H:3]([OH:18])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.C(N(C(C)C)CC)(C)C.[C:28](Cl)([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29].O>ClCCl>[CH2:31]([O:30][C:28]([NH:1][CH2:2][C@@H:3]([OH:18])[CH2:4][N:5]1[CH2:6][CH2:7][N:8]([C:11]([O-:13])=[O:12])[CH2:9][CH2:10]1)=[O:29])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[CH2:31]([O:30][C:28]([NH:1][CH2:2][C@@H:3]([OH:18])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH2:7][CH2:6]1)=[O:29])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 7009319Tert-butyl 4-[(2R)-3-amino-2-hydroxy-propyl]piperazine-1-carboxylate

생성물 2

HCID 68107180tert-butyl 4-[(2R)-3-benzyloxycarbonylamino-2-hydroxy-propyl]piperazine-1-carboxylate수율 52.6%HCID 1317313064-[(2R)-3-benzyloxycarbonylamino-2-hydroxy-propyl]piperazine-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

The crude compound tert-butyl 4-[(2R)-3-amino-2-hydroxy-propyl]piperazine-1-carboxylate 20b (4.50 g, 17.40 mmol) was dissolved in 80 mL of dichloromethane in an ice-water bath followed by the addition of diisopropylethylamine (2.50 g, 19.10 mmol) and dropwise addition of 20 mL of a solution of carbobenzoxy chloride (2 g, 19.10 mmol) in dichloromethane successively, stirred for 12 hours. The resulting mixture was added with 20 mL of water and stirred for 10 minutes. The reaction solution was concentrated under reduced pressure, added with 100 mL of water and extracted with ethyl acetate (100 mL×3). The combined organic phase was washed with saturated sodium chloride solution (50 mL×3), then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound tert-butyl 4-[(2R)-3-benzyloxycarbonylamino-2-hydroxy-propyl]piperazine-1-carboxylate 20c (1.80 g, yield: 26.0%) as a light yellow oil.

후처리

  1. stirringstirred for 10 minutes
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionadded with 100 mL of water
  4. extractionextracted with ethyl acetate (100 mL×3)
  5. washThe combined organic phase was washed with saturated sodium chloride solution (50 mL×3)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-6cac3d13c35d4c93905f1c540a43e3e8
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691822B2

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