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Methane → 3-[(Acetyloxy)methyl]-7-[[2-carboethoxy-2-(1-pyrryl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid

HRID 26317
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HRID 26317 반응식
[N:1]1([CH:6]([C:10]([OH:12])=O)[C:7]([OH:9])=[O:8])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH2:13](N(CC)CC)[CH3:14].C.[C:21]([O:24][CH2:25][C:26]1[CH2:33][S:32][CH:31]2[N:28]([C:29](=[O:35])[CH:30]2[NH2:34])[C:27]=1[C:36]([OH:38])=[O:37])(=[O:23])[CH3:22]>CN(C)C=O.C(Cl)(Cl)Cl>[C:21]([O:24][CH2:25][C:26]1[CH2:33][S:32][CH:31]2[N:28]([C:29](=[O:35])[CH:30]2[NH:34][C:10](=[O:12])[CH:6]([C:7]([O:9][CH2:13][CH3:14])=[O:8])[N:1]2[CH:2]=[CH:3][CH:4]=[CH:5]2)[C:27]=1[C:36]([OH:38])=[O:37])(=[O:23])[CH3:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 297MethaneHCID 8471TriethylamineHCID 137293-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 197854272-(1H-pyrrol-1-yl)malonic acid

생성물 1

HCID 706050383-[(Acetyloxy)methyl]-7-[[2-carboethoxy-2-(1-pyrryl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid수율 19%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

실험 절차

A solution of the monoethyl ester of 2(1-pyrryl) propanedioic acid (1 g., 5.07 mM) and 0.87 g. (5.2 mM) of N, N"-carbonyldiimidazole in 10 ml of dimethylformamide is stirred at room temperature for one hour. In a second flask, 3[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (1.37 g, 5.07 mM) is dissolved in 35 ml of chloroform upon the addition of 2.05 g (20.3 mM) of triethylamine and is stirred under nitrogen for 30 minutes in the presence of Linde 44 molecular sieves. The two solutions are combined and the mixture stirred for 4 hours after the addition of 0.5 g of charcoal. The reaction mixture is filtered, concentrated by flash evaporation and the residue is dissolved in 25 ml of water and washed several times with ether. The aqueous phase is covered with 50 ml of ethyl acetate and is then acidified to pH of 2.5 with 6 N hydrochloric acid. A small amount of solid is removed by filtration and the organic phase is separated, dried and concentrated to 5 ml. The title compound is obtained as a powder (425 mg., 19% yield) upon addition of the ethyl acetate solution to hexane.

후처리

  1. stirringthe mixture stirred for 4 hours
  2. filtrationThe reaction mixture is filtered
  3. concentrationconcentrated by flash evaporation
  4. dissolutionthe residue is dissolved in 25 ml of water
  5. washwashed several times with ether
  6. customA small amount of solid is removed by filtration
  7. customthe organic phase is separated
  8. customdried
  9. concentrationconcentrated to 5 ml

출처 및 근거

ORD 기록
ord-159163d686044074918c63f16e83fe3d
출처 데이터셋
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04148998

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