Triphenylphosphine → 3-Triphenylmethyl-5-([4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl]methyl)oxazolidine-2,4-dione

HRID 1595481Notes

Reaction equation

HRID 1595481 reaction equation
[C:1]1([C:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:8]2[C:12](=[O:13])[CH:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)[O:10][C:9]2=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:35][S:36]([O:39][C:40]1[CH:45]=[CH:44][C:43]([CH2:46][CH2:47]O)=[CH:42][CH:41]=1)(=[O:38])=[O:37].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:29]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:8]2[C:12](=[O:13])[CH:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:47][CH2:46][C:43]4[CH:42]=[CH:41][C:40]([O:39][S:36]([CH3:35])(=[O:37])=[O:38])=[CH:45][CH:44]=4)=[CH:17][CH:16]=3)[O:10][C:9]2=[O:22])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 149136625-(4-Hydroxybenzyl)-3-trityloxazolidine-2,4-dioneHCID 229887694-(2-Hydroxyethyl)phenyl methanesulfonate

Product 1

HCID 217049903-Triphenylmethyl-5-([4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl]methyl)oxazolidine-2,4-dioneYield 53.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.28 g (0.623 mmole) 3-triphenylmethyl-5-([4-hydroxyphenyl]methyl)oxazolidine-2,4-dione was under argon atmosphere added to a cooled solution of 0.148 g (0.685 mmole) 2-[4-(methylsulfonyloxy)phenyl]-1-ethanol, 0.173 g (0.685 mmole) 1,1′-(azodicarbonyl)-dipiperidine and 0.18 g (0.685 mmole) triphenylphosphine in 6 ml dichloromethane. After stirring for 3 hours the reaction mixture was filtered and the crude product was purified by chromatography on silica gel using heptane:ethyl acetate (2:2) as eluent to give 0.215 g (yield 53%) of 3-triphenylmethyl-5-([4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl]methyl)oxazolidine-2,4-dione.

Workup

  1. filtrationwas filtered
  2. customthe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c2422fb6f19945ae9a56404682df8ab8
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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