Methanol → HCID 15029531, compound

HRID 1534312Notes

Reaction equation

HRID 1534312 reaction equation
[OH:1][C:2]([CH2:4][O:5][NH:6][C:7](=[O:26])[CH:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[C:23]([Cl:24])=[CH:22][C:21]([Cl:25])=[CH:20][N:19]=2)=[CH:13][CH:12]=1)[CH3:9])=O.[N+](=[CH2:29])=[N-].[CH3:30][OH:31]>>[CH3:30][O:31][C:2]([CH2:4][O:5][N:6]([CH3:29])[C:7](=[O:26])[CH:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[C:23]([Cl:24])=[CH:22][C:21]([Cl:25])=[CH:20][N:19]=2)=[CH:13][CH:12]=1)[CH3:9])=[O:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 9550DiazomethaneHCID 15029529N-hydroxycarbonylmethoxy-2-[4-(3,5-dichloro-2-pyridyloxy)phenoxy]propionamide

Product 1

HCID 15029531HCID 15029531, compound

Procedure

To a solution of N-hydroxycarbonylmethoxy-2-[4-(3,5-dichloro-2-pyridyloxy)phenoxy]propionamide (Compound No. 37 as obtained in Example 3) (0.38 g) in methanol (1 ml), there was added an etheral solution of diazomethane until the yellow color remained, and the resultant mixture was allowed to stand for 10 minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluent: 88% hexane :12% ethyl acetate) to give N-methoxycarbonylmethoxy-N-methyl-2-[4-(3,5-dichloro-2-pyridyloxy)phenoxy]propionamide (0.35 g). Yield, 86%.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel chromatography (eluent: 88% hexane :12% ethyl acetate)

Sources & evidence

ORD record
ord-433b977421394548bb40fc871dcd23cf
Source dataset
uspto-grants-1992_02
Patent number
US05089043

Reaction notes

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