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 67933ノート

反応式

HRID 67933 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 ; νmax (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, NCH 2 CH2S) 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-cb2699af0cfe40fd84feeb54304f8f6b
出典データセット
uspto-grants-1982_08
特許番号
US04347181

反応ノート

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