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7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid → 7-tert.-Butoxycarbonylamino-2-carboxy-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene

HRID 1660390
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HRID 1660390 반응식
[NH2:1][CH:2]1[C:9](=[O:10])[N:8]2[CH:3]1[S:4][CH2:5][C:6]([CH3:14])=[C:7]2[C:11]([OH:13])=[O:12].[C:15](=O)([O:21]C(C)(C)C)[O:16][C:17]([CH3:20])([CH3:19])[CH3:18]>C(=O)(O)[O-].[Na+].O.O1CCOCC1>[C:17]([O:16][C:15]([NH:1][CH:2]1[C:9](=[O:10])[N:8]2[CH:3]1[S:4][CH2:5][C:6]([CH3:14])=[C:7]2[C:11]([OH:13])=[O:12])=[O:21])([CH3:20])([CH3:19])[CH3:18]
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참가 물질

6

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HCID 18837-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

생성물 1

HCID 128967587-tert.-Butoxycarbonylamino-2-carboxy-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene수율 89.3%

시약·촉매·용매 3

HCID 962Water용매HCID 312751,4-Dioxane
용매
2회
HCID 516892Sodium Bicarbonate용매

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온도
25 °C

실험 절차

7-Amino-2-carboxy-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (371 g) is dissolved in a solution of sodium bicarbonate (307 g) in a mixture of distilled water (2 liters) and dioxane (2 liters). A solution of di-tert.-butyl carbonate (421 g) in dioxane (2 liters) is added in the course of 10 minutes. The reaction mixture is stirred for 48 hours at 25° C. The suspension obtained is concentrated under reduced pressure (20 mm Hg) at 50° C. to a residual volume of about 2 liters, and is then diluted with ethyl acetate (1 liter) and distilled water (2 liters). The aqueous phase is decanted, washed with ethyl acetate (500 cc) and acidified to pH 2 with 6 N hydrochloric acid in the presence of ethyl acetate (1500 cc). The aqueous phase is extracted with ethyl acetate (2×1 liter). The combined organic phases are washed with a saturated sodium chloride solution (2×250 cc) and dried over sodium sulphate. After filtration, the solvent is evaporated under reduced pressure (20 mm Hg) at 50° C. 7-tert.-Butoxycarbonylamino-2-carboxy-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (486 g) is obtained in the form of yellow crystals (m.p.=190° C., with decomposition).

후처리

  1. customThe suspension obtained
  2. concentrationis concentrated under reduced pressure (20 mm Hg) at 50° C. to a residual volume of about 2 liters
  3. additionis then diluted with ethyl acetate (1 liter)
  4. distillationdistilled water (2 liters)
  5. customThe aqueous phase is decanted
  6. washwashed with ethyl acetate (500 cc)
  7. extractionThe aqueous phase is extracted with ethyl acetate (2×1 liter)
  8. washThe combined organic phases are washed with a saturated sodium chloride solution (2×250 cc)
  9. dry with materialdried over sodium sulphate
  10. filtrationAfter filtration
  11. customthe solvent is evaporated under reduced pressure (20 mm Hg) at 50° C

출처 및 근거

ORD 기록
ord-7034206d02f2485c8963423f3e79dc86
출처 데이터셋
uspto-grants-1981_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04307230

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