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Sodium Bicarbonate → 7-Amino-2-benzhydryloxycarbonyl-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene

HRID 1660395
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HRID 1660395 반응식
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:13]([O:26][C:27]([C:29]1[N:30]2[CH:33]([S:34][CH2:35][C:36]=1[CH:37]=[CH:38][O:39][S:40]([C:43]1[CH:49]=[CH:48][C:46]([CH3:47])=[CH:45][CH:44]=1)(=[O:42])=[O:41])[CH:32]([NH:50]C(OC(C)(C)C)=O)[C:31]2=[O:58])=[O:28])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[NH2:50][CH:32]1[C:31](=[O:58])[N:30]2[CH:33]1[S:34][CH2:35][C:36]([CH:37]=[CH:38][O:39][S:40]([C:43]1[CH:49]=[CH:48][C:46]([CH3:47])=[CH:45][CH:44]=1)(=[O:42])=[O:41])=[C:29]2[C:27]([O:26][CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:28]
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참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 540314202-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene

생성물 1

HCID 542754077-Amino-2-benzhydryloxycarbonyl-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene수율 90.8%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매
2회

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온도
35 °C

실험 절차

A solution of p-toluenesulphonic acid hydrate (3.49 g) in acetonitrile (25 cc) is added dropwise, in the course of 25 minutes, to a solution, at 35° C., of 2-benzhydryloxycarbonyl-7-tert.-butoxycarbonylamino-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (E-form) (6.1 g) in acetonitrile (75 cc). The mixture is stirred for 45 minutes at 35° C. and is then poured into a saturated sodium bicarbonate solution (500 cc). After 30 minutes' contact, with stirring, the mixture is extracted with ethyl acetate (500 cc) and the organic phase is washed with water (100 cc), dried over sodium sulphate, filtered and concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa). 7-Amino-2-benzhydryloxycarbonyl-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (E-form) (4.7 g) is obtained in the form of a brown froth.

후처리

  1. waitAfter 30 minutes' contact
  2. stirringwith stirring
  3. extractionthe mixture is extracted with ethyl acetate (500 cc)
  4. washthe organic phase is washed with water (100 cc)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa)

출처 및 근거

ORD 기록
ord-89d41b5aca8a4f998d61796482110721
출처 데이터셋
uspto-grants-1981_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04307230

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