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Tris(furan-2-yl)phosphane → HCID 14167873, 화합물

HRID 1608371
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HRID 1608371 반응식
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:42](=[O:43])[N:13]3[C:14]([C:26]([O:28][CH:29]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])=[C:15](OS(C(F)(F)F)(=O)=O)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:44][O:45][C:46]1[CH:51]=[CH:50][C:49]([Sn](CCCC)(CCCC)CCCC)=[CH:48][CH:47]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>CN1CCCC1=O.C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd]>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:42](=[O:43])[N:13]3[C:14]([C:26]([O:28][CH:29]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:27])=[C:15]([C:49]4[CH:50]=[CH:51][C:46]([O:45][CH3:44])=[CH:47][CH:48]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 2762547TRIBUTYL(4-METHOXYPHENYL)STANNANEHCID 14167862HCID 14167862, 화합물

생성물 1

HCID 14167873HCID 14167873, 화합물수율 57%

시약·촉매·용매 4

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladium촉매
HCID 3007855
Zincchloride
촉매
HCID 8857Ethyl Acetate용매
HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

A mixture of 0.1029 g ((0.000163 mole) of diphenylmethyl 7-phenylacetamido-3-(trifluoromethylsulfonyloxy)-3-cephem- -4-carboxylate, 0.0775 g (0.000195 mole) of (p-methoxyphenyl)tri-n-butylstannane, 0.044 g (0.00032 mole) of zinc chloride and 0.00378 g (0.000016 mole) of tri(2-furyl)-phosphine in 4 mL of dry 1-methyl-2-pyrrolidinone, under an argon atmosphere, was degassed for 30 seconds. Then 0.0047 g (0.000008 mole) of palladium(0) bis(dibenzylidene acetone) was added all at once. The reaction mix was stirred at 50° for 5.5 hrs and room temperature for 16 hrs. The reaction mix was then diluted with ethyl acetate and the organic solution washed with dilute ammonium chloride. The ethyl acetate was removed at reduced pressure and replaced with acetonitrile. The organic phase was washed with n-pentane and the acetonitrile removed at reduced pressure. The residue was chromatographed on silica gel to yield 0.0548 g (57%) of diphenylmethyl 7-phenylacetamido-3-(p-methoxyphenyl)-3cephem-4-carboxylate. The nuclear magnetic resonance spectrum was consistent for the desired structure.

후처리

  1. customunder an argon atmosphere, was degassed for 30 seconds
  2. additionThe reaction mix
  3. additionThe reaction mix
  4. washthe organic solution washed with dilute ammonium chloride
  5. customThe ethyl acetate was removed at reduced pressure
  6. washThe organic phase was washed with n-pentane
  7. customthe acetonitrile removed at reduced pressure
  8. customThe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-c3b842485f144005991ce157d4e260cc
출처 데이터셋
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04870168

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