Triethylamine → Phenyl 1-(3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo(3,2,0)hept-2-en-6-yl)-1-(p-nitrobenzyloxycarbonyl)-prop-1-en-2-yl phenylphosphonate

HRID 1155426Notes

Reaction equation

HRID 1155426 reaction equation
[O:1]([CH2:8][C:9]1[S:15][CH:14]2[CH:11]([C:12](=[O:33])[N:13]2[C:16](=[C:30]([OH:32])[CH3:31])[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[O:18])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:41]1([P:47](Cl)(=[O:55])[O:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>O1CCCC1>[C:41]1([P:47](=[O:55])([O:32][C:30]([CH3:31])=[C:16]([N:13]2[C:12](=[O:33])[CH:11]3[CH:14]2[S:15][C:9]([CH2:8][O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:10]3)[C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)=[O:18])[O:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 99269Phenyl P-phenylphosphonochloridateHCID 70504145p-Nitrobenzyl alpha-[3-phenoxymethyl-7-oxo4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-alpha-(1-hydroxyethylidene)acetate

Product 1

HCID 54307816Phenyl 1-(3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo(3,2,0)hept-2-en-6-yl)-1-(p-nitrobenzyloxycarbonyl)-prop-1-en-2-yl phenylphosphonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of p-nitrobenzyl α-(3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo(3,2,0)hept-2-en-6-yl)-α-(1-hydroxyethylidene)acetate (4.69 g) in tetrahydrofuran (60 ml.) under a nitrogen atmosphere at 0° C. was added triethylamine (1.6 ml.) followed by phenyl phenylphosphonochloridate (2.91 g). After stirring for 3 hours at 20° C., the tetrahydrofuran was evaporated and the residue dissolved in dichloromethane. The resulting solution was washed with 1% hydrochloric acid and then water, dried with magnesium sulphate and evapoated to give the title compound as a pale yellow friable foam in essentially quantitative yield. TLC (silica)Rf 0.64 (ethyl acetate). NMR δCDCl3 2.60 (m, 3H), 3.70-4.67 (m, 2H), 5.15 (s, 2H), 5.57-5.87 (m, 2H) and 6.6-8.17 (m, 19H).

Workup

  1. customthe tetrahydrofuran was evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washThe resulting solution was washed with 1% hydrochloric acid
  4. dry with materialwater, dried with magnesium sulphate

Sources & evidence

ORD record
ord-54a45128c83047fa9b2606a3d33d013d
Source dataset
uspto-grants-1981_11
Patent number
US04301280

Reaction notes

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