Tributylphosphine → HCID 15383951, compound

HRID 1901699Notes

Reaction equation

HRID 1901699 reaction equation
C(P(CCCC)CCCC)CCC.[Cl:14][C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][CH:32]=1)[O:18][CH2:19][C@@H:20]1[O:24][C:23](=[O:25])[N:22]([C@H:26]([CH3:29])[CH2:27][OH:28])[CH2:21]1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.O[C:52]1[CH:84]=[CH:83][C:55]([CH2:56][CH:57]2[S:61][C:60](=[O:62])[N:59]([C:63]([C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=3)([C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)[C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[C:58]2=[O:82])=[CH:54][CH:53]=1>C1C=CC=CC=1>[Cl:14][C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][CH:32]=1)[O:18][CH2:19][C@@H:20]1[O:24][C:23](=[O:25])[N:22]([C@H:26]([CH3:29])[CH2:27][O:28][C:52]2[CH:84]=[CH:83][C:55]([CH2:56][CH:57]3[S:61][C:60](=[O:62])[N:59]([C:63]([C:76]4[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=4)([C:70]4[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=4)[C:64]4[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=4)[C:58]3=[O:82])=[CH:54][CH:53]=2)[CH2:21]1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dioneHCID 677415862-Oxazolidinone, 5-[(3-chlorophenoxy)methyl]-3-(2-hydroxy-1-methylethyl)-, [R-(R*,R*)]-

Product 1

HCID 15383951HCID 15383951, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A procedure similar to that described in Preparation 6 was repeated, except that 526 mg of tributylphosphine, 25 ml of anhydrous benzene, 900 mg of 2(R)-[5(R)-(3-chlorophenoxymethyl)-2-oxooxazolidin-3-yl]propanol (prepared as described in Preparation 44), 656 mg of azodicarbonyldipiperidine and 1.21 g of 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione were used, to give 0.65 g of the title compound, melting at 74° C. to 81° C. and having [α]D =-29.0° (methanol, c=1.000).

Workup

  1. customA procedure similar to that described in Preparation 6

Sources & evidence

ORD record
ord-676eb8a37b274db7913a37fafece26f5
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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