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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Water → 2-Acetoxymethoxycarbonyl-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene

HRID 258782
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HRID 258782 반응식
[Na].[C:2]([C:5]1[N:6]2[CH:9]([S:10][CH2:11][C:12]=1[CH2:13][S:14][C:15]1[N:19]([CH3:20])[N:18]=[N:17][N:16]=1)[CH:8]([NH:21][C:22](=[O:30])[CH2:23][C:24]1[S:25][C:26](=[O:29])[S:27][CH:28]=1)[C:7]2=[O:31])([OH:4])=[O:3].[C:32]([O:35][CH2:36]I)(=[O:34])[CH3:33].O>CN(C)C=O>[C:32]([O:35][CH2:36][O:3][C:2]([C:5]1[N:6]2[CH:9]([S:10][CH2:11][C:12]=1[CH2:13][S:14][C:15]1[N:19]([CH3:20])[N:18]=[N:17][N:16]=1)[CH:8]([NH:21][C:22](=[O:30])[CH2:23][C:24]1[S:25][C:26](=[O:29])[S:27][CH:28]=1)[C:7]2=[O:31])=[O:4])(=[O:34])[CH3:33]
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6

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HCID 962WaterHCID 5360545SodiumHCID 11820084Iodomethyl acetateHCID 214264602-Carboxy-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene

생성물 1

HCID 214264782-Acetoxymethoxycarbonyl-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene
수율 53.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
5 °C

실험 절차

The sodium salt of 2-carboxy-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (5.08 g.) is dissolved in dimethylformamide (100 cc.) at 5° C. A solution of iodomethyl acetate (2 g.) in dimethylformamide (10 cc.) is added to this solution and the reaction mixture is stirred for 10 minutes at 5° C. It is then poured into water (500 cc.) and extracted twice with ethyl acetate (200 cc.). The combined organic phases are washed with water (100 cc.), saturated sodium bicarbonate solution (100 cc.), a 5% sodium bisulphite solution (100 cc.) and a saturated sodium chloride solution (100 cc.). The organic phase is dried over magnesium sulphate, filtered in the presence of decolourising charcoal and concentrated to dryness under reduced pressure (15 mm Hg). This gives a white product (5 g.) which is recrystallised from acetonitrile (50 cc.). 2-Acetoxymethoxycarbonyl-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (3 g.) is thus obtained as white crystals m.p. 154° C.

후처리

  1. extractionextracted twice with ethyl acetate (200 cc.)
  2. washThe combined organic phases are washed with water (100 cc.), saturated sodium bicarbonate solution (100 cc.)
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered in the presence of decolourising charcoal
  5. concentrationconcentrated to dryness under reduced pressure (15 mm Hg)
  6. customThis gives a white product (5 g.) which
  7. customis recrystallised from acetonitrile (50 cc.)

출처 및 근거

ORD 기록
ord-584b794bc89a436a87b0503b882a8328
출처 데이터셋
uspto-grants-1977_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04034090

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