Trifluoroacetic acid → 2-(4-(Benzyloxy)-3-tert-butylbenzamido)acetic acid

HRID 2225267Notes

Reaction equation

HRID 2225267 reaction equation
[CH2:1]([O:8][C:9]1[CH:25]=[CH:24][C:12]([C:13]([NH:15][CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])=[O:14])=[CH:11][C:10]=1[C:26]([CH3:29])([CH3:28])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:25]=[CH:24][C:12]([C:13]([NH:15][CH2:16][C:17]([OH:19])=[O:18])=[O:14])=[CH:11][C:10]=1[C:26]([CH3:29])([CH3:28])[CH3:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69285477Tert-butyl 2-(4-(benzyloxy)-3-tert-butylbenzamido)acetate

Product 1

HCID 692860352-(4-(Benzyloxy)-3-tert-butylbenzamido)acetic acidYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(4-(benzyloxy)-3-tert-butylbenzamido)acetate (3.37 g, 8.48 mmol) in CH2Cl2 (100 mL) at 0° C. was added TFA (10 mL) and the mixture was stirred at room temperature under nitrogen atmosphere for 10 h. The reaction mixture was concentrated in vacuo to dryness to give 2-(4-(benzyloxy)-3-tert-butylbenzamido)acetic acid (2.50 g, 86%) as a white powder: mp 172-174° C.; 1H NMR (300 MHz, CD3OD) δ 7.86 (s, 1H), 7.74-7.70 (m, 1H), 7.50-7.30 (m, 5H), 7.10-7.05 (m, 1H), 5.18 (s, 2H), 4.07 (s, 2H), 1.41 (s, 9H); IR (film) 3497, 3062, 3031, 2931, 2865, 1447, 1289, 1139, 1085, 1062 cm−1; MS found: (M+H)+=342.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-4f75140001d749d89eb1fdafedc0be9a
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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