Phosphate → HCID 131721068, compound

HRID 342285Notes

Reaction equation

HRID 342285 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([S:18][C@H:19]2[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=3)=[O:25])[CH2:20]2)=[O:17])[NH:13][C:12]1=[O:37])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[N+:45]([C:48]1[CH:58]=[CH:57][C:51]([CH2:52][O:53][CH2:54][CH2:55]Cl)=[CH:50][CH:49]=1)([O-:47])=[O:46].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@H:19]2[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=3)=[O:25])[CH2:20]2)=[O:17])[N:13]([CH2:55][CH2:54][O:53][CH2:52][C:51]2[CH:57]=[CH:58][C:48]([N+:45]([O-:47])=[O:46])=[CH:49][CH:50]=2)[C:12]1=[O:37])[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 1061PhosphateHCID 8471TriethylamineHCID 54554880HCID 54554880, compoundHCID 88672339HCID 88672339, compound

Product 1

HCID 131721068HCID 131721068, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

57.7 mg (0.105 mmole) of (3S, 4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-4-([(S)-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinone and 33 mg (0.33 mmole) of triethylamine were dissolved in 3 ml of methylene chloride. To the solution were added 73 mg (0.30 mmole) of p-nitrobenzyloxyethyl chloride, with ice-cooling under a nitrogen atmosphere. The mixture was stirred for 1 hour and then poured into a 0.1M phosphate buffer solution (pH 7.2). The organic layer was separated and washed with a saturated aqueous solution of sodium chloride. The solvent was distilled off and the residue was purified by column chromatography through 1.3 g of silica gel, to give 67.8 mg (yield 83%) of the desired product as an oil from the fraction eluted with mixtures of benzene and ethyl acetate in volume ratios from 12:1 to 4:1.

Workup

  1. temperaturewith ice-cooling under a nitrogen atmosphere
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by column chromatography through 1.3 g of silica gel

Sources & evidence

ORD record
ord-5e9d6070719d4ba582b0d1c1f2dbfa02
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

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