Triphenylphosphine → Methyl N-[(benzyloxy)carbonyl]-L-valinate

HRID 1578535Notes

Reaction equation

HRID 1578535 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COSC1C=CC=CC=1.C1C=C(SSC2N=CC=CC=2)N=CC=1>C(Cl)Cl>[CH3:19][O:17][C:16](=[O:18])[C@H:12]([CH:13]([CH3:15])[CH3:14])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 650932,2'-Dipyridyl disulfideHCID 318902(Methoxysulfanyl)benzeneHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 10967417Methyl N-[(benzyloxy)carbonyl]-L-valinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.51 g. of N-benzyloxycarbonyl-L-valine, 2.62 g. of triphenyl phosphine, 1.40 g. of benzenesulfenic acid methyl ester, 1.10 g. of 2,2'-dipyridyl disulfide and 50 ml. of methylene chloride is stirred at room temperature for 5 hours. The reaction mixture is treated with the same procedure as in Example 1 (1) to give 2.30 g. of the desired product.

Workup

  1. additionA mixture of 2.51 g
  2. customto give 2.30 g

Sources & evidence

ORD record
ord-b7e239cf59d64d0391f2deb601c17831
Source dataset
uspto-grants-1976_02
Patent number
US03937718

Reaction notes

Loading…