Imidazole → methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-[(tert-butyldiphenylsilyl)oxy]propanoate

HRID 1711196

반응식

HRID 1711196 반응식
[CH3:1][O:2][C:3](=[O:15])[C@H:4]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][OH:6].N1C=CN=C1.[Si:21](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH3:1][O:2][C:3](=[O:15])[C@H:4]([NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:5][O:6][Si:21]([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 377723N-Boc-D-serine methyl ester

생성물 1

HCID 11762248methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-[(tert-butyldiphenylsilyl)oxy]propanoate수율 72.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(R)-2-tert-Butoxycarbonylamino-3-hydroxy-propionic acid methyl ester (2.2 mg, 10 mmol) was dissolved in THF (20 ml). Imidazole (818 mg, 12 mmol) and TBDPS chloride (2.9 ml, 11 mmol) were added. The mixture was stirred at rt overnight. The mixture was then partitioned between CH2Cl2 and water (30 ml/30 ml). The organic layer was concentrated and the residue was purified by column chromatography (6/1, Hexanes/EtOAc) to give (R)-2-tert-butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid methyl ester (3.3 g, 72%).

후처리

  1. customThe mixture was then partitioned between CH2Cl2 and water (30 ml/30 ml)
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by column chromatography (6/1, Hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-c430f316576c46f58d1614a10a8bcfcf
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790747B2

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