Triethyl Phosphate → HCID 13219914, compound

HRID 342283Notes

Reaction equation

HRID 342283 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)[N:13]([CH2:25][CH2:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=2)[C:12]1=[O:38])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].P(OCC)(OCC)(OCC)=[O:40]>C1(C)C=CC=CC=1>[Si:1]([O:8][C@@H:9]([C@H:11]1[C:12](=[O:38])[N:13]2[C:25]([C:26]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=3)=[O:40])=[C:16]([S:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:15][C@H:14]12)[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6535Triethyl PhosphateHCID 131721067HCID 131721067, compound

Product 1

HCID 13219914HCID 13219914, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 114 mg (0.194 mmole) of (3S, 4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-1-(p-nitrobenzyloxyethyl)-4-[(phenylthio)carbonylmethyl]-2-azetidinone, 258 mg (1.55 mmole) of triethyl phosphate and 10 ml of toluene was stirred at 100° C. for 18 hours under a nitrogen atmosphere. The solvent was distilled off, and the residue was purified by the procedure described in Example 5, to give 95 mg (yield 88%) of the title product , in the form of crystals.

Workup

  1. distillationThe solvent was distilled off
  2. customthe residue was purified by the procedure

Sources & evidence

ORD record
ord-37e539cc2d024a268739bf812b1a92bc
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

Loading…