Triphenylphosphine → HCID 14696294, compound

HRID 1200139Notes

Reaction equation

HRID 1200139 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:19]([OH:21])=O)[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][C:23]([NH2:31])([CH3:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=C(SSC2N=CC=CC=2)N=CC=1>C(Cl)Cl>[CH3:22][C:23]([NH:31][C:19](=[O:21])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:10][O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([CH3:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 650932,2'-Dipyridyl disulfideHCID 68509CumylamineHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

Product 1

HCID 14696294HCID 14696294, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

11.0 g of powdery N-(t-butoxycarbonyl)-O-benzyl-L-serine were added to 200 ml of a methylene chloride solution containing 5.0 g of α,α-dimethylbenzylamine and 10.0 g of triphenylphosphine. 20 ml of a methylene chloride solution containing 8.2 g of 2,2'-dipyridyl disulfide were then added dropwise. The mixture was then stirred for 1 hour at room temperature, after which the solvent was distilled off under reduced pressure and the residue was subjected to silica gel column chromatography. The title compound was obtained as an oil from the fraction eluted with a 2:1 by volume mixture of ethyl acetate and hexane. Yield 9.2 g.

Workup

  1. additionwere then added dropwise
  2. distillationafter which the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3553447fded0426b91ae717cbfc8f022
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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