Tributylphosphine → HCID 22854986, compound

HRID 1648459Notes

Reaction equation

HRID 1648459 reaction equation
[OH:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][CH:7]2[S:11][C:10](=[O:12])[N:9]([C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]2=[O:32])=[CH:4][CH:3]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[C:66]([O:70][C:71]([NH:73][C@H:74]([CH2:77][CH:78]([CH3:80])[CH3:79])[CH2:75]O)=[O:72])([CH3:69])([CH3:68])[CH3:67]>C1C=CC=CC=1>[C:66]([O:70][C:71]([NH:73][C@H:74]([CH2:77][CH:78]([CH3:80])[CH3:79])[CH2:75][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[S:11][C:10](=[O:12])[N:9]([C:13]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:8]2=[O:32])=[CH:33][CH:34]=1)=[O:72])([CH3:68])([CH3:69])[CH3:67]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dioneHCID 16211316tert-Butyl [(2R)-1-hydroxy-4-methylpentan-2-yl]carbamate

Product 1

HCID 22854986HCID 22854986, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.1 g of 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione [prepared as described in Preparation 11] were added to a mixture of 2.28 g of 1,1'-azodicarbonyl-dipiperidine, 3.34 ml of tributylphosphine and 100 ml of anhydrous benzene. The resulting mixture was stirred at room temperature for one and a half hours, after which 2 g of 2(R)-t-butoxycarbonylamino-4-methylpentanol [prepared as described in Preparation 15] were added. The mixture was then stirred for a further five hours at the same temperature. At the end of this time, insolubles were filtered off and the filtrate was concentrated. The resulting residue was then purified by column chromatography through silica gel, using a 1:4 by volume mixture of ethyl acetate and hexane as the eluent, to obtain 1.05 g of the title compound, having an Rf=0.54 (thin layer chromatography on silica gel, using a 1:4 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. stirringThe mixture was then stirred for a further five hours at the same temperature
  2. filtrationAt the end of this time, insolubles were filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe resulting residue was then purified by column chromatography through silica gel
  5. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-4afb409839bf484bb07ff27e4ee86b7b
Source dataset
uspto-grants-1995_07
Patent number
US05436257

Reaction notes

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