Tributylphosphine → 5-{4-[3-(5-Phenoxymethyl-2-oxooxazolidin-3-yl)propoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dione

HRID 1901754Notes

Reaction equation

HRID 1901754 reaction equation
C(P(CCCC)CCCC)CCC.[OH:14][C:15]1[CH:47]=[CH:46][C:18]([CH2:19][CH:20]2[S:24][C:23](=[O:25])[N:22]([C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]2=[O:45])=[CH:17][CH:16]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[O:66]([CH2:73][CH:74]1[O:78][C:77](=[O:79])[N:76]([CH2:80][CH2:81][CH2:82]O)[CH2:75]1)[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1>C1C=CC=CC=1>[O:66]([CH2:73][CH:74]1[O:78][C:77](=[O:79])[N:76]([CH2:80][CH2:81][CH2:82][O:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:19][CH:20]3[S:24][C:23](=[O:25])[N:22]([C:26]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:21]3=[O:45])=[CH:46][CH:47]=2)[CH2:75]1)[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dioneHCID 214747813-(5-Phenoxymethyl-2-oxooxazolidin-3-yl)propanol

Product 1

HCID 214747515-{4-[3-(5-Phenoxymethyl-2-oxooxazolidin-3-yl)propoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dioneYield 55.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A procedure similar to that described in Preparation 6 was repeated, except that 1.29 g of tributylphosphine, 30 ml of anhydrous benzene, 2.98 g of 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione, 1.61 g of azodicarbonyldipiperidine and 1.33 g of 3-(5-phenoxymethyl-2-oxooxazolidin-3-yl)propanol (prepared as described in Preparation 114) were used, to give 2.04 g of the title compound, melting at 70° C. to 73° C.

Workup

  1. customA procedure similar to that described in Preparation 6

Sources & evidence

ORD record
ord-3286f50403aa468cbf833b1985a39491
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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