Diphenyl chlorophosphate → p-Nitrobenzyl 2-azidocarbapen-2-em-3-carboxylate

HRID 847196Notes

Reaction equation

HRID 847196 reaction equation
P(Cl)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.O=[C:19]1[CH:23]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=2)=[O:25])[N:22]2[C:37](=[O:39])[CH2:38][C@H:21]2[CH2:20]1.C(N(C(C)C)CC)(C)C.[N-:49]=[N+:50]=[N-:51].[K+]>CN(C)C1C=CN=CC=1.C(#N)C>[N:49]([C:19]1[CH2:20][C@@H:21]2[CH2:38][C:37](=[O:39])[N:22]2[C:23]=1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1)=[O:25])=[N+:50]=[N-:51]

Participants

7

Reactant 4

HCID 75654Diphenyl chlorophosphateHCID 81531DiisopropylethylamineHCID 10290740Potassium azideHCID 131715742p-Nitrobenzyl 2-oxo-carbapenam-3-carboxylate

Product 1

HCID 131715741p-Nitrobenzyl 2-azidocarbapen-2-em-3-carboxylateYield 19.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

Diphenyl chlorophosphate (10.9 microliter, 52.6 micromol) was added to a stirred, 0° C. solution of a p-nitrobenzyl 2-oxo-carbapenam-3-carboxylate (15.4 mg, 50.6 micromol), 4-dimethylaminopyridine (1.3 mg, 11 micromol), and diisopropylethylamine (10.4 microliter, 59.7 micromol) in anhydrous acetonitrile (500 microliter). After 5 min., potassium azide (12.6 mg, 155 micromol), and 1, 4, 7, 10, 13, 16-hexaoxacyclooctadecane (13.3 mg, 50.3 micromol) were added. After an additional 5 min. the mixture was washed three times with water, dried over anhydrous magnesium sulfate, filtered, and evaporated under vacuum. The residue was applied to one 20 cm×20 cm 250 micron silica gel preparative thin layer chromatography plate and developed with diethyl ether. Elution with ethyl acetate and evaporation of the eluate under vacuum provided 3.2 mg (19%) p-nitrobenzyl 2-azido-carbapen-2-em-3-carboxylate.

Workup

  1. washAfter an additional 5 min. the mixture was washed three times with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. washElution
  6. customwith ethyl acetate and evaporation of the eluate under vacuum

Sources & evidence

ORD record
ord-33c3112a12e9434595fd710d1931f177
Source dataset
uspto-grants-1992_08
Patent number
US05140030

Reaction notes

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