Imidazole → HCID 14629888, 화합물

HRID 495603노트

반응식

HRID 495603 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH2:16][OH:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH2:16][O:17][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5314177Cbz-D-prolinol

생성물 1

HCID 14629888HCID 14629888, 화합물수율 90.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of D1 (9.70 g, 0.04 mol), imidazole (1.05 eq., 2.95 g) and tert-butyldimethylsilyl chloride (1.1 eq., 6.22 g) in DMF (dry, 50 ml) was stirred overnight at ambient temperature. Solvent was removed under reduced pressure and the residue partitioned between Et2O and water. The aqueous phase was separated and the organic phase washed with dilute HCl (0.5M, 2×100 ml), followed by water (2×100 ml) and the organic phase was then dried (anhydrous MgSO4), filtered and concentrated under reduced pressure to afford an oil (12.70 g). This was used in the next step without purification.

후처리

  1. customSolvent was removed under reduced pressure
  2. customthe residue partitioned between Et2O and water
  3. customThe aqueous phase was separated
  4. washthe organic phase washed with dilute HCl (0.5M, 2×100 ml)
  5. dry with materialthe organic phase was then dried (anhydrous MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f50dd52f6f494823b6494a092f53e6b3
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06939891B2

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