Imidazole → HCID 57947507、化合物

HRID 416334ノート

反応式

HRID 416334 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:17][OH:18])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].C(OCC)C>CN(C=O)C.[Cl-].[Na+].O>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:17][O:18][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:3])([CH3:2])[CH3:4]

参加物

7

反応物 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 57947757HCID 57947757、化合物

生成物 1

HCID 57947507HCID 57947507、化合物収率 92%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of (S)-methyl 5-(tert-butoxycarbonylamino)-6-hydroxyhexanoate (12 g, 46 mmol) in DMF (100 mL) was added imidazole (7.8 g, 115 mmol, 2.5 equiv.). TBS-Cl (8.25 g, 55 mmol, 1.2 equiv.) was then added in 3 portions. The reaction was complete in 30 min. Diethyl ether (200 mL) and brine (300 mL) were added to the reaction solution. The organic layer was further washed with brine (300 mL), dried, and concentrated to give (S)-methyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsilyloxy)hexanoate (15.9 g, 92%) as a colorless oil. LRMS (M-Boc+H+) m/z 276.1.

後処理

  1. washThe organic layer was further washed with brine (300 mL)
  2. customdried
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-fb2ce7506ac04ba98c29523d493e0816
出典データセット
uspto-grants-2012_01
特許番号
US08088793B2

反応ノート

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