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Water → HCID 57073292, 화합물

HRID 619708
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HRID 619708 반응식
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH2:10]([O:17][C:18]([NH:20][C@H:21]1[C@H:24]([O:25][C:26](=O)[CH3:27])[NH:23][C:22]1=[O:29])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C1COCC1>[CH2:10]([O:17][C:18]([NH:20][C@H:21]1[C@H:24]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:23][C:22]1=[O:29])=[O:19])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1.[CH2:10]([O:17][C:18]([NH:20][C@H:21]1[C@@H:24]([O:25][C:26]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:27]=2)[NH:23][C:22]1=[O:29])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 996PhenolHCID 14798Sodium HydroxideHCID 13124491HCID 13124491, 화합물

생성물 2

HCID 57073292HCID 57073292, 화합물HCID 57174922HCID 57174922, 화합물

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

반응 조건

온도
0 °C

실험 절차

To a solution of phenol (2.82 g 30 mmole) in THF (30 ml) and 1N NaOH (26 ml, 26 mmole), (3S, 4S)-3-benzyloxycarbonylamino-4-acetoxy-azetidin-2-one (5.56 g, 20 mmole) in THF (40 ml) and H2O (20 ml) is added at 0° C. The mixture is stirred at 0° C for 1 hour and then at room temperature for 30 min. After removal of solvent, the residue is dissolved in ethyl acetate, washed with water, brine and dried over sodium sulphate. After removal of solvent, the residue is purified by silica gel column chromatography using hexane-ethyl acetate as eluent. 2.75 g of (3S, 4S)-3-benzyloxycarbonylamino-4-phenoxy-azetidin-2-one (A), 890 mg of (3S, 4R)-3-benzyloxycarbonylamino-4-phenoxy-azetidin-2-one (B) and 1.08 g of a mixture of (A) and (B) is obtained.

후처리

  1. waitat room temperature for 30 min
  2. customAfter removal of solvent
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulphate
  6. customAfter removal of solvent
  7. customthe residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-7d2a6508254449269e856a6bf57e5bdb
출처 데이터셋
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05959123

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