Trifluoroacetic acid → 2-(4-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-3-(nicotinamidomethyl)phenyl)acetic acid

HRID 453539Notes

Reaction equation

HRID 453539 reaction equation
[Cl:1][C:2]1[CH:43]=[CH:42][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:41]=[CH:40][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[CH:18][C:17]=3[CH2:30][NH:31][C:32](=[O:39])[C:33]3[CH:38]=[CH:37][CH:36]=[N:35][CH:34]=3)=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][C:17]=3[CH2:30][NH:31][C:32](=[O:39])[C:33]3[CH:38]=[CH:37][CH:36]=[N:35][CH:34]=3)=[CH:40][CH:41]=2)=[O:10])=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68466216Tert-butyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-(nicotinamidomethyl)phenyl)acetate

Product 1

HCID 594031642-(4-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-3-(nicotinamidomethyl)phenyl)acetic acidYield 114.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-(nicotinamidomethyl)phenyl)acetate (0.005 g, 0.008 mmol) in dichloromethane (1.0 ml) was added TFA (1.0 ml) and the reaction was stirred at ambient temperature. After 1 hour the reaction was concentrated to give 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-(nicotinamidomethyl)phenyl)acetic acid (0.005 g). MS −449.1 [M—CO2H].

Workup

  1. concentrationAfter 1 hour the reaction was concentrated

Sources & evidence

ORD record
ord-e9d8d0831d4f4fdcbf820f0022f7b746
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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