Phosphate → HCID 131721067, compound

HRID 342282Notes

Reaction equation

HRID 342282 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])[NH:13][C:12]1=[O:25])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[N+:33]([C:36]1[CH:46]=[CH:45][C:39]([CH2:40][O:41][CH2:42][CH2:43]Cl)=[CH:38][CH:37]=1)([O-:35])=[O:34].P([O-])([O-])([O-])=O>C(Cl)Cl>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])[N:13]([CH2:43][CH2:42][O:41][CH2:40][C:39]2[CH:45]=[CH:46][C:36]([N+:33]([O-:35])=[O:34])=[CH:37][CH:38]=2)[C:12]1=[O:25])[CH3:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1061PhosphateHCID 8471TriethylamineHCID 13219837HCID 13219837, compoundHCID 54554880HCID 54554880, compound

Product 1

HCID 131721067HCID 131721067, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

747 mg (1.97 mmole) of (3S, 4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-4-[(phenylthio)carbonylmethyl]-2-azetidinone and 398 mg (3.94mmole) of triethylamine were dissolved in 20 ml of methylene chloride. To the solution were added 960 mg (3.94 mmole) of p-nitrobenzyloxyethyl chloride, with ice cooling under a stream of nitrogen. The mixture was stirred for 2 hours and then a 0.1M phosphate buffer solution (pH 7.2) was added to the reaction mixture to complete the reaction. The organic layer was separated and washed with water, after which it was dried. The solvent was distilled off and the resulting residue was purified by column chromatography through 15 g of silica gel, to give 1,032 mg (yield 89%) of the desired product as an oil from the fractions eluted with mixtures of hexane and ethyl acetate in volume ratios from 6:1 to 3:1.

Workup

  1. customthe reaction
  2. customThe organic layer was separated
  3. washwashed with water
  4. customafter which it was dried
  5. distillationThe solvent was distilled off
  6. customthe resulting residue was purified by column chromatography through 15 g of silica gel

Sources & evidence

ORD record
ord-6c3dbc4af1d544898a81bdceb372510f
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

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