Sodium Hydroxide → HCID 59643218, compound

HRID 2251540Notes

Reaction equation

[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:18]([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][N:31]=2)[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[CH:12][CH:11]=1)([CH3:8])[C:3]([O:5]CC)=[O:4].[OH-].[Na+]>>[CH3:8][C:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][N:18]([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][N:31]=2)[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:22][CH:21]=2)=[CH:14][CH:15]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 59643238HCID 59643238, compound

Product 1

HCID 59643218HCID 59643218, compoundYield 49%

Procedure

Ethyl 2-methyl-2-[4-(2-{(5-nitropyridin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]propanoate (80 mg) was hydrolyzed with NaOH as per general procedure H. Purification by radial chromatography (1–5% methanol-dichloromethane gradient) followed by crystallization from dichloromethane-hexane afforded the title compound as a white solid (37 mg; 49% yield).

Workup

customPurification by radial chromatography (1–5% methanol-dichloromethane gradient)
customfollowed by crystallization from dichloromethane-hexane

Sources & evidence

ORD record: ord-612fa647a0b948f383e2f1eb59f4189d
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319104B2

Reaction notes

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