Sodium Hydroxide → HCID 10164392, compound

HRID 892292Notes

Reaction equation

HRID 892292 reaction equation
C([O:3][C:4](=[O:25])[C:5]([NH:7][C:8]1[CH:13]=[C:12]([Br:14])[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=2)=[C:10]([Br:24])[CH:9]=1)=[O:6])C.[OH-].[Na+]>CO>[Br:14][C:12]1[CH:13]=[C:8]([NH:7][C:5](=[O:6])[C:4]([OH:25])=[O:3])[CH:9]=[C:10]([Br:24])[C:11]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22242279HCID 22242279, compound

Product 1

HCID 10164392HCID 10164392, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl-N-[3,5-dibromo-4-(3-bromobenzyloxy)phenyl]oxamate (18 mg) was dissolved in methanol (1 mL) and treated with sodium hydroxide (IN, 6–8 equivalents). After stirring over night at room temperature, the reaction mixture was acidified to pH 5. The mixture was purified on semi-preperative HPLC using the same conditions as described for Examples 27, 28 and 30. This gave 7.8 mg (46%) of N-[3,5-dibromo-4-(3-bromobenzyloxy)phenyl]oxamic acid. MS: m/z 508.0 (M+−1).

Workup

  1. customThe mixture was purified on semi-preperative HPLC

Sources & evidence

ORD record
ord-58193ded21354b7cbbbc4afff4496e73
Source dataset
uspto-grants-2006_02
Patent number
US07005538B1

Reaction notes

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