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Sodium Chloride → (6R,7R)-7-benzyloxycarbonylamino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one

HRID 851409
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인쇄 미리보기

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HRID 851409 반응식
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C@@H:15]([CH2:16][CH2:17][OH:18])[NH:14][C:13]1=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:22](OC)([CH3:24])[CH3:23].B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C:13](=[O:19])[N:14]2[C@@H:15]1[CH2:16][CH2:17][O:18][C:22]2([CH3:24])[CH3:23])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

7

반응물 5

HCID 5234Sodium ChlorideHCID 64952,2-DimethoxypropaneHCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 13744723(3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)azetidin-2-one

생성물 1

HCID 13744719(6R,7R)-7-benzyloxycarbonylamino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a suspension of (3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)azetidin-2-one (735 mg) in methylene chloride (30 ml) were added 2,2-dimethoxypropane (0.513 ml) and boron trifluoride etherate (0.026 ml) at 0° C. The mixture was stirred for 10 minutes at 0° C. and for 5 hours at ambient temperature. The reaction mixture was poured into a mixture of methylene chloride (30 ml) and aqueous sodium bicarbonate and sodium chloride (1:1). The organic layer was separated and the aqueous layer was extracted with methylene chloride (20 ml). The combined organic layers were washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (16 g) eluting with a mixture of methylene chloride and acetone (10:1-5:1) to give (6R,7R)-7-benzyloxycarbonylamino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one (753 mg) as an oil.

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with methylene chloride (20 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel (16 g)
  7. washeluting with a mixture of methylene chloride and acetone (10:1-5:1)

출처 및 근거

ORD 기록
ord-090fce9dcfdd4a61b2ad7d4efd68a9a6
출처 데이터셋
uspto-grants-1983_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04383945

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