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 1155422노트

반응식

HRID 1155422 반응식
[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]

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

반응 조건

온도
20 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6d53ddf0615640bdbbce8bb2ef2e5776
출처 데이터셋
uspto-grants-1981_11
특허 번호
US04301280

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