Methyl 4-(4-chloro-3-ethoxy-5-(pentan-3-yloxy)benzamido)benzoate → 4-(4-Chloro-3-ethoxy-5-(pentan-3-yloxy)benzamido)benzoic acid
Reaction equation
[Cl:1][C:2]1[C:20]([O:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)=[O:7])=[CH:4][C:3]=1[O:27][CH2:28][CH3:29]>O1CCOCC1>[Cl:1][C:2]1[C:20]([O:21][CH:22]([CH2:23][CH3:24])[CH2:25][CH3:26])=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=2)=[O:7])=[CH:4][C:3]=1[O:27][CH2:28][CH3:29]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
4-(4-Chloro-3-ethoxy-5-(pentan-3-yloxy)benzamido)benzoic acid (AAA-114) (50 mg, 65%) was prepared from methyl 4-(4-chloro-3-ethoxy-5-(pentan-3-yloxy)benzamido)benzoate (11) (76 mg, 0.18 mmol) using a procedure essentially the same as in step (ii) for AAA-001 except that dioxane (2 mL) was used instead of THF and the mixture was stirred at 50° C. for 2 h: m/z 406 [M+H]+ (ES+), 404 [M−H]− (ES−); 1H NMR (400 MHz, DMSO-d6) δ: 12.79 (1H, br s), 10.46 (1H, s), 7.99-7.93 (2H, m), 7.91-7.82 (2H, m), 7.27 (2H, dd), 4.46 (1H, quin), 4.20 (2H, q), 1.71-1.64 (4H, m), 1.39 (3H, t), 0.93 (6H, t).
Sources & evidence
- ORD record
- ord-c45f3ed467804ba0b3e78a233807bdb4
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447028B2
Reaction notes
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