1,5-Diazabicyclo(5,4,0)undec-5-ene → Benzyl 3-(2-acetamidoethylsulphinyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 27737ノート

反応式

HRID 27737 の反応式
[C:1]([NH:4][CH2:5][CH2:6][S:7]([C:9]1(Cl)[CH2:15][CH:14]2[N:11]([C:12](=[O:16])[CH2:13]2)[CH:10]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:8])(=[O:3])[CH3:2].N12CCCCC1C=NCCC2>C(OCC)(=O)C>[C:1]([NH:4][CH2:5][CH2:6][S:7]([C:9]1[CH2:15][CH:14]2[N:11]([C:12](=[O:16])[CH2:13]2)[C:10]=1[C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])=[O:8])(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 20526351HCID 20526351、化合物

生成物 1

HCID 20526356Benzyl 3-(2-acetamidoethylsulphinyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate収率 76.8%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A solution of benzyl 3-(2-acetamidoethylsulphinyl)-3-chloro-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate (62) (0.010 g) in ethyl acetate (1 ml) was treated with 1,5-diazabicyclo[5.4.0]undec-5-ene (0.0037 g) under an argon atmosphere. It was stirred at room temperature for 15 minutes and then washed with brine and dried over sodium sulphate. The solution was concentrated to give benzyl 3-(2-acetamidoethylsulphinyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (63) (0.007 g) as a colourless gum; νmax (CHCl3) 3400, 2980, 2920, 1795, 1920, 1670, 1600 and 1515 cm-1 ; λmax (ethanol) 305 nm; τ (CDCl3) 2.5-2.8 (5H, m, phenyl), 4.76 (2H, s, benzyl CH2), 5.6-5.9 (1H, m, C5-H), 6.3-7.3 (8H, m, C4-H2, C6-H2, NCH2CH2S) and 8.14 (3H, s, COCH3).

後処理

  1. washwashed with brine
  2. dry with materialdried over sodium sulphate
  3. concentrationThe solution was concentrated

出典と根拠

ORDレコード
ord-b37376fee30041db945d9951e42ba314
出典データセット
uspto-grants-1980_09
特許番号
US04223038

反応ノート

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