Carbon Dioxide → HCID 54211819, compound

HRID 1658021Notes

Reaction equation

HRID 1658021 reaction equation
C1([Li])C=CC=CC=1.C(=O)=O.[CH:11](=[N:18][CH2:19][P:20](=[O:35])([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl[C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=1)=[O:38]>O1CCCC1>[CH:11](=[N:18][CH:19]([P:20]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:35])[C:37]([O:39][CH2:40][C:41]1[CH:42]=[CH:43][C:44]([N+:47]([O-:49])=[O:48])=[CH:45][CH:46]=1)=[O:38])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 782054-Nitrobenzyl chloroformateHCID 54329991HCID 54329991, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 54211819HCID 54211819, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Phenyllithium (45 ml of a 2.3 M solution in 7:3 benzene-ether) in added to a dry-ice-cooled, stirring solution of diphenyl N-benzylidene-aminomethylphosphonate (35.1 g) in anhydrous tetrahydrofuran (500 ml). After having been stirred for 15 minutes at -78° under a nitrogen atmosphere, the solution is treated dropwise over 1 hour with p-nitrobenzyl chloroformate (10.8 g) in tetrahydrofuran (100 ml). The resulting solution is stirred an additional 2 hours at -78°, then allowed to warm to 5° over a period of 30 minutes. Evaporation of the solvent under reduced pressure leaves a residue which is partitioned between ethyl ether (500 ml) and 0.5 pH 3 phosphate buffer (200 ml). The aqueous phase is separated and extracted with ethyl ether (2 × 100 ml). The combined ethereal solution is washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography of the residue on silica gel affords p-nitrobenzyl N-benzylidene-α-amino-diphenylphosphonoacetate as well as starting material.

Workup

  1. temperaturecooled
  2. stirringThe resulting solution is stirred an additional 2 hours at -78°
  3. temperatureto warm to 5° over a period of 30 minutes
  4. customEvaporation of the solvent under reduced pressure
  5. customleaves a residue which
  6. customis partitioned between ethyl ether (500 ml) and 0.5 pH 3 phosphate buffer (200 ml)
  7. customThe aqueous phase is separated
  8. extractionextracted with ethyl ether (2 × 100 ml)
  9. washThe combined ethereal solution is washed with saturated brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52d791efb0414995bb8970bb54d9e1b6
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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