Trifluoroacetic acid → O-methoxymethyl-N-methyl-beta-benzoyloxytyrosine methyl ester

HRID 1648178Notes

Reaction equation

HRID 1648178 reaction equation
[CH3:1][O:2][C:3](=[O:37])[C@H:4]([CH:17]([O:28][C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][O:26][CH3:27])=[CH:20][CH:19]=1)[N:5]([CH3:16])SC1C=CC=CC=1[N+]([O-])=O.C1(S)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][O:2][C:3](=[O:37])[C@H:4]([CH:17]([O:28][C:29](=[O:36])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][O:26][CH3:27])=[CH:20][CH:19]=1)[NH:5][CH3:16]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7969ThiophenolHCID 516892Sodium BicarbonateHCID 54000197O-methoxymethyl-N-methyl-N-(2-nitrophenylthio)-beta-benzoyloxytyrosine methyl ester

Product 1

HCID 53867281O-methoxymethyl-N-methyl-beta-benzoyloxytyrosine methyl esterYield 9.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of O-methoxymethyl-N-methyl-N-(2-nitrophenylthio)-β-benzoyloxytyrosine methyl ester (threo isomer) (4.94 g) in dichloromethane (50 ml) were added thiophenol (4.8 ml) and trifluoroacetic acid (2.5 ml) at 0° C. After stirring for 30 minutes, sodium bicarbonate aqueous solution was added to the mixture. The organic layer was washed with sodium bicarbonate aqueous solution and brine. After evaporating, the residue was put on a column of silica gel (MERCK 7734, 100 g) and eluted with 5% methanol in chloroform to give O-methoxymethyl-N-methyl-β-benzoyloxytyrosine methyl ester (threo isomer) (0.32 g).

Workup

  1. washThe organic layer was washed with sodium bicarbonate aqueous solution and brine
  2. customAfter evaporating
  3. washeluted with 5% methanol in chloroform

Sources & evidence

ORD record
ord-c5d0c30df5ac46ec97f649a03af17fbe
Source dataset
uspto-grants-1995_07
Patent number
US05436140

Reaction notes

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