Methyl morpholine oxide → 4-Formyl-2-phenylbenzoyl methionine methyl ester

HRID 325216Notes

Reaction equation

HRID 325216 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH2:22][CH2:23][S:24][CH3:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][C:8]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C[N+]1([O-])CCOCC1.C(Cl)Cl.C(#N)C>C(OCC)C.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH2:22][CH2:23][S:24][CH3:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][C:8]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 82029Methyl morpholine oxideHCID 20622833[4-Hydroxymethyl-2-phenylbenzoyl]methionine methyl esterHCID 21877088Acetonitrile methylene chloride

Product 1

HCID 105712674-Formyl-2-phenylbenzoyl methionine methyl ester

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of the resultant alcohol from Example 16D (1.0 equivalent), N-methylmorpholine-N-oxide (1.5 equivalents), molecular sieves, and a catalytic amount of TPAP is stirred in a CH2Cl2/acetonitrile mixture until the reaction is judged complete by TLC analysis. The mixture is diluted with ethyl ether and filtered through SiO2. The product is purified by chromatography on silica gel.

Workup

  1. filtrationfiltered through SiO2
  2. customThe product is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-da779eed196c4ddf89a83ca47f77ade7
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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