Imidazole → HCID 57947507, 화합물

HRID 416334노트

반응식

HRID 416334 반응식
[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]

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 57947757HCID 57947757, 화합물

생성물 1

HCID 57947507HCID 57947507, 화합물수율 92%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-fb2ce7506ac04ba98c29523d493e0816
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088793B2

반응 노트

불러오는 중…