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

HRID 1711196

反応式

HRID 1711196 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(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%).

後処理

  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)

出典と根拠

ORDレコード
ord-c430f316576c46f58d1614a10a8bcfcf
出典データセット
uspto-grants-2010_09
特許番号
US07790747B2

関連ノート

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