Phosphate → HCID 86753532, compound

HRID 342290Notes

Reaction equation

HRID 342290 reaction equation
[N+:1]([C:4]1[CH:31]=[CH:30][C:7]([CH2:8][O:9][C:10]([O:12][C@@H:13]([C@@H:15]2[C@@H:18]([CH2:19][C:20]([S:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:21])[NH:17][C:16]2=[O:29])[CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.[N+:41]([C:44]1[CH:54]=[CH:53][C:47]([CH2:48][O:49][CH2:50][CH2:51]Cl)=[CH:46][CH:45]=1)([O-:43])=[O:42].P([O-])([O-])([O-])=O>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([O:12][C@@H:13]([C@@H:15]2[C@@H:18]([CH2:19][C:20]([S:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:21])[N:17]([CH2:51][CH2:50][O:49][CH2:48][C:47]3[CH:53]=[CH:54][C:44]([N+:41]([O-:43])=[O:42])=[CH:45][CH:46]=3)[C:16]2=[O:29])[CH3:14])=[O:11])=[CH:30][CH:31]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 1061PhosphateHCID 81531Diisopropylethylamine2×HCID 54554880HCID 54554880, compound2×HCID 86753533HCID 86753533, compound

Product 1

HCID 86753532HCID 86753532, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.00 g (2.25 mmole) of (3S, 4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-4-[(phenylthio)carbonyl-methyl]-2-azetidinone was dissolved in 20 ml of methylene chloride. To the solutiion were added 350 mg (2.71 mmole) of diisopropylethylamine and then 660 mg (2.71 mmole) of p-nitrobenzyloxyethyl chloride, with stirring at 0° C. After 15 minutes, a further 230 mg (1.78 mmole) of diisopropylethylamine and 433 mg (1.78 mmole) of p-nitrobenzyloxyethyl chloride were added, and the mixture was stirred at that temperature for 15 minutes. After completion of the reaction, 30 ml of a 0.1M phosphate buffer solution (pH 7.1) was added to the reaction mixture and the organic layer was separated. The aqueous lager was extracted with chloroform. The organic layer was combined with the chloroform extract and then the solvent was distilled from the mixture. The residue was dissolved in 50 ml of a 1:1 by volume mixture of benzene and ethyl acetate, washed successively with 0.02N hydrochloric acid, water, a 5% w/v aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulphate. The solvent was distilled off, to afford 1.47 g (yield 100%) of the title product as crystals which were recrystallized from a mixture of benzene and ethyl acetate, to afford the pure product melting at 129°-130° C.

Workup

  1. additionwas added to the reaction mixture
  2. customthe organic layer was separated
  3. extractionThe aqueous lager was extracted with chloroform
  4. extractionextract
  5. distillationthe solvent was distilled from the mixture
  6. dissolutionThe residue was dissolved in 50 ml of a 1:1 by volume mixture of benzene and ethyl acetate
  7. washwashed successively with 0.02N hydrochloric acid, water
  8. dry with materiala 5% w/v aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulphate
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-25ed23ea4b4e46a4aed318059d6ff60f
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

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