Tributylphosphine → HCID 15383950, compound

HRID 1901696Notes

Reaction equation

HRID 1901696 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 67741583HCID 67741583, compound

Product 1

HCID 15383950HCID 15383950, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A procedure similar to that described in Preparation 6 was repeated, except that 405 mg of tributylphosphine, 25 ml of anhydrous benzene, 700 mg of 2(S)-[5(S)-(3-chlorophenoxymethyl)-2-oxooxazolidin-3-yl]propanol (prepared as described in Preparation 40), 505 mg of azodicarbonyldipiperidine and 745 mg of 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione were used, to give 340 mg of the title compound, melting at 80° C. to 84° C. and having [α]D =+25.9° (methanol, c=0.96).

Workup

  1. customA procedure similar to that described in Preparation 6

Sources & evidence

ORD record
ord-94f51e1e5abc477fad586202a43e8e75
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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