Methanol → (2S,3R)-methyl 3-azido-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

HRID 1783438노트

반응식

HRID 1783438 반응식
[N:1]([C@H:4]1[C:7](=[O:8])[N:6]([Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[C@@H:5]1[C:16]([OH:18])=[O:17])=[N+:2]=[N-:3].CO.[CH2:21]1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:1]([C@H:4]1[C:7](=[O:8])[N:6]([Si:9]([C:12]([CH3:14])([CH3:15])[CH3:13])([CH3:11])[CH3:10])[C@@H:5]1[C:16]([O:18][CH3:21])=[O:17])=[N+:2]=[N-:3]

참가 물질

6

반응물 3

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 13712291(2S,3R)-1-t-butyldimethylsilyl-3-azido-4-oxo-2-azetidinecarboxylic acid

생성물 1

HCID 57589884(2S,3R)-methyl 3-azido-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of crude 131 (1.58 g) in CH2Cl2 (25 mL) was added methanol (0.26 mL, 6.43 mmol). DCC (1.45 g, 7.02 mmol) and catalytic DMAP. The solution was stirred at room temperature overnight. The solution was then filtered through Celite and concentrated in vacuo. The crude product was purified by silica gel column chromatography, eluting with 20% EtOAc in hexanes, to yield pure 132.

후처리

  1. filtrationThe solution was then filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by silica gel column chromatography
  4. washeluting with 20% EtOAc in hexanes
  5. customto yield pure 132

출처 및 근거

ORD 기록
ord-635b4696e07342a98a906857c2e01f9a
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07501404B2

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