Diazomethane → O-methoxymethyl-N-methyl-N-(2-nitrophenylthio)-beta-hydroxytyrosine methyl ester

HRID 1648176Notes

Reaction equation

HRID 1648176 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:28]=[CH:27][C:8]([CH:9]([OH:26])[C@@H:10]([C:23]([OH:25])=[O:24])[N:11]([CH3:22])[S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])=[CH:7][CH:6]=1.[N+](=[CH2:31])=[N-]>C(OCC)(=O)C.C(OCC)C>[CH3:31][O:24][C:23](=[O:25])[C@H:10]([CH:9]([OH:26])[C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:28][CH:27]=1)[N:11]([CH3:22])[S:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 54196694O-methoxymethyl-N-methyl-N-(2-nitrophenylthio)-beta-hydroxytyrosine

Product 1

HCID 54118395O-methoxymethyl-N-methyl-N-(2-nitrophenylthio)-beta-hydroxytyrosine methyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of O-methoxymethyl-N-methyl-N-(2-nitrophenylthio)-β-hydroxytyrosine (20.0 g) in ethyl acetate (100 ml) was added diazomethane in diethyl ether (80 ml). After stirring for 10 minutes, the solvent was removed in vacuo. The residue was put on a silica gel column (MERCK 7734:500 g) and eluted with chloroform to give O-methoxymethyl-N-methyl-N-(2-nitrophenylthio)-β-hydroxytyrosine methyl ester. (threo isomer: 8.82 g, erythro isomer: 6.63 g)

Workup

  1. customthe solvent was removed in vacuo
  2. washeluted with chloroform

Sources & evidence

ORD record
ord-3ed6d02fdf434f218607135f955db35a
Source dataset
uspto-grants-1995_07
Patent number
US05436140

Reaction notes

Loading…