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 1155422Notes

Reaction equation

HRID 1155422 reaction equation
[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]

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
20 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6d53ddf0615640bdbbce8bb2ef2e5776
Source dataset
uspto-grants-1981_11
Patent number
US04301280

Reaction notes

Loading…