Water → Diethyl 1-(3-benzyl-7-oxo-4-thia-2,6-diazabicyclo [3,2,0]hept-2-en-6-yl)-1-(p-nitrobenzyloxycarbonyl)-prop-1-en-2-yl phosphate

HRID 1155422ノート

反応式

HRID 1155422 の反応式
[CH2:1]([C:8]1[S:14][CH:13]2[CH:10]([C:11](=[O:32])[N:12]2[C:15](=[C:29]([OH:31])[CH3:30])[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:17])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:38][CH3:39])CC)C.C([P:42](Cl)(CC)=[O:43])C.[OH2:47].[C:48]([O:51]CC)(=O)[CH3:49]>CN(C)C1C=CN=CC=1>[P:42]([O:31][C:29]([CH3:30])=[C:15]([N:12]1[C:11](=[O:32])[CH:10]2[CH:13]1[S:14][C:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[N:9]2)[C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1)=[O:17])([O:43][CH2:38][CH3:39])([O:51][CH2:48][CH3:49])=[O:47]

参加物

7

反応物 5

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 5195381Diethylphosphinoyl chlorideHCID 70503680p-Nitrobenzyl alpha-(3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl)-alpha-(1-hydroxyethylidene)acetate

生成物 1

HCID 53693443Diethyl 1-(3-benzyl-7-oxo-4-thia-2,6-diazabicyclo [3,2,0]hept-2-en-6-yl)-1-(p-nitrobenzyloxycarbonyl)-prop-1-en-2-yl phosphate

試薬・触媒・溶媒 1

HCID 142844-(Dimethylamino)pyridine触媒

反応条件

温度
20 °C

実験手順

To a solution of p-nitrobenzyl α-(3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl)-α-(1-hydroxyethylidene)acetate (4.53 g) containing 4-dimethylaminopyridine (0.1 g) in ethyl acetate (50 ml) under a nitrogen atmosphere at 20° C. was added triethylamine (1.53 ml) followed by diethylphosphoryl chloride (1.59 ml) dropwise. The reaction mixture was stirred at 20° C. for 3 hours. Water (40 ml) was added and the organic layer was separated, washed with water (20 ml) and saturated sodium chloride solution (20 ml), dried with magnesium sulphate and carbon treated, filtered and evaporated to give the title compound as a yellow viscous oil in essentially quantitative yield. TLC (silica) Rf 0.17 (dichloromethane/ethyl acetate 15:2). The product was a mixture of geometric isomers (ca. 2:1) about the enol phosphate double bond. NMR δCDCl3 1.11-1.60 (m, 6H), 1.98+2.60 (d, 3H), 3.73-4.65 (m, 6H), 5.22-5.42 (m, 2H), 5.88-6.28 (m, 2H) and 7.25-7.80 and 8.18-8.58 (m, 9H).

後処理

  1. customthe organic layer was separated
  2. washwashed with water (20 ml) and saturated sodium chloride solution (20 ml)
  3. dry with materialdried with magnesium sulphate and carbon
  4. additiontreated
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-6d53ddf0615640bdbbce8bb2ef2e5776
出典データセット
uspto-grants-1981_11
特許番号
US04301280

反応ノート

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