HCID 69384357, compound → HCID 69385550, compound

HRID 860961Notes

Reaction equation

HRID 860961 reaction equation
[CH3:1][N:2]([C:7](=[O:31])[C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][C:16]2[CH:21]=[C:20]([CH:22]([CH3:24])[CH3:23])[C:19]([O:25][CH3:26])=[C:18]([N+:27]([O-])=O)[CH:17]=2)=[C:10]([Cl:30])[CH:9]=1)[CH2:3][C:4]([OH:6])=[O:5]>C(OCC)(=O)C.O=[Pt]=O>[CH3:1][N:2]([C:7](=[O:31])[C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][C:16]2[CH:21]=[C:20]([CH:22]([CH3:24])[CH3:23])[C:19]([O:25][CH3:26])=[C:18]([NH2:27])[CH:17]=2)=[C:10]([Cl:30])[CH:9]=1)[CH2:3][C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 69384357HCID 69384357, compound

Product 1

HCID 69385550HCID 69385550, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl-N-[3,5-dichloro-4-(5-isopropyl-4-methoxy-3-nitro-phenoxy)benzoyl]glycine (380 mg, 0.81 mmol) and PtO2 (40 mg) in ethyl acetate (10 mL) was stirred at room temperature under hydrogen (atmospheric pressure) for 24 h. Pt catalyst was removed by filtration through celite and the filtrate was concentrated, which was purified on column (silica gel, n-heptane/ethyl acetate, gradient elution from 98:2 to 60:40) to give 320 mg (89%) of methyl-N-[3,5-dichloro-4-(3-amino-5-isopropyl-4-methoxyphenoxy)benzoyl]glycine.

Workup

  1. customPt catalyst was removed by filtration through celite
  2. concentrationthe filtrate was concentrated
  3. customwhich was purified on column (silica gel, n-heptane/ethyl acetate, gradient elution from 98:2 to 60:40)

Sources & evidence

ORD record
ord-f80c9c4382194526b8236499ecafc532
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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