Water → Diphenylmethyl 7-t-Butoxycarbonyl-3-(Z)-1-propenyl-3-cephem-4-carboxylate

HRID 373351

反応式

HRID 373351 の反応式
[C:1]([O:5][C:6]([CH:8]1[C:38](=[O:39])[N:10]2[C:11]([C:22]([O:24][CH:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[C:12](SC3N(C)N=NN=3)[CH2:13][S:14][C@H:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:40]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:45]=CC=C[CH:41]=1.C(/[Sn](CCCC)(CCCC)CCCC)=C/C.O>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Cl-].[Zn+2].[Cl-].C(OCC)(=O)C>[C:1]([O:5][C:6]([CH:8]1[C:38](=[O:39])[N:10]2[C:11]([C:22]([O:24][CH:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[O:23])=[C:12](/[CH:41]=[CH:40]\[CH3:45])[CH2:13][S:14][C@H:9]12)=[O:7])([CH3:3])([CH3:4])[CH3:2]

参加物

9

反応物 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 10914524(Z)-Tri-n-butyl(1-propenyl)tinHCID 67918291Diphenylmethyl 7-t-butoxycarbonyl-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)thio]-3-cephem-4-carboxylate

生成物 1

HCID 131717638Diphenylmethyl 7-t-Butoxycarbonyl-3-(Z)-1-propenyl-3-cephem-4-carboxylate収率 139.8%

試薬・触媒・溶媒 4

HCID 3007855Zincchloride触媒HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of diphenylmethyl 7-t-butoxycarbonyl-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)thio]-3-cephem-4-carboxylate (IId, 0.125 g, 0.000215 mole), bis(dibenzylideneacetone)palladium (0.0062 g, 0.00001075 mole), triphenyl phosphine (0.0084 g, 0.000032 mole), zinc chloride (0.0586 g, 0.00043 mole) and Z-1-propenyltributyl stannane (0.071 g, 0.000215 mole) in dry tetrahydrofuran (2 mL) was refluxed under argon atmosphere for 20 h. After no further conversion of starting compound IId took place, water and ethyl acetate were added. The organic phase was separated, dried and concentrated. The crude product dissolved in acetonitrile and the acetonitrile solution was washed three times with equal volumes of pentane. Flash chromatography with 20% ethyl acetate in hexane gave the title product (0.022 g, 20%) as a foam. Also recovered was 0.0435g (34.8%) of starting compound IId.

後処理

  1. temperaturewas refluxed under argon atmosphere for 20 h
  2. customThe organic phase was separated
  3. customdried
  4. concentrationconcentrated
  5. dissolutionThe crude product dissolved in acetonitrile
  6. washthe acetonitrile solution was washed three times with equal volumes of pentane

出典と根拠

ORDレコード
ord-5aea3cdc63fc46858d5c54d168ca7d17
出典データセット
uspto-grants-1992_11
特許番号
US05162521

関連ノート

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