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Tris(furan-2-yl)phosphane → HCID 14167873、化合物

HRID 1608371
ノート
印刷プレビュー

反応式

HRID 1608371 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 2762547TRIBUTYL(4-METHOXYPHENYL)STANNANEHCID 14167862HCID 14167862、化合物

生成物 1

HCID 14167873HCID 14167873、化合物収率 57%

試薬・触媒・溶媒 4

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladium触媒
HCID 3007855
Zincchloride
触媒
HCID 8857Ethyl Acetate溶媒
HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c3b842485f144005991ce157d4e260cc
出典データセット
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04870168

反応ノート

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