N-(4-Hydroxybenzoyl)glycine tert-butyl ester → N-(4-{2-[4-(Trifluoromethyl)phenyl]ethoxy}benzoyl)glycine

HRID 456310Notes

Reaction equation

HRID 456310 reaction equation
C([O:5][C:6](=[O:18])[CH2:7][NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)(C)(C)C.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28]O)=[CH:23][CH:22]=1>>[F:19][C:20]([F:30])([F:31])[C:21]1[CH:22]=[CH:23][C:24]([CH2:27][CH2:28][O:16][C:13]2[CH:12]=[CH:11][C:10]([C:9]([NH:8][CH2:7][C:6]([OH:5])=[O:18])=[O:17])=[CH:15][CH:14]=2)=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 10682169N-(4-Hydroxybenzoyl)glycine tert-butyl esterHCID 112755102-(4-(Trifluoromethyl)phenyl)ethan-1-ol

Product 1

HCID 66812342N-(4-{2-[4-(Trifluoromethyl)phenyl]ethoxy}benzoyl)glycineYield 75.7%

Procedure

The same reaction as in Example 1 (1b) was conducted using N-(4-hydroxybenzoyl)glycine tert-butyl ester (251 mg, 1.00 mmol) prepared in Example 1 (1a) and 2-[4-(trifluoromethyl)phenyl]ethanol (209 mg, 1.10 mmol) prepared according to the method disclosed in the document (J. Med. Chem., (2002), 45, 4321-4335) to give 278 mg of the title compound (white powder, yield: quantitative).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-a1f9f2e42754473b90ee7322f98d56b3
Source dataset
uspto-grants-2013_07
Patent number
US08497397B2

Reaction notes

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