Methyl 4-(4-chloro-3,5-diisopropoxybenzamido)benzoate → 4-(4-Chloro-3,5-diisopropoxybenzamido)benzoic acid

HRID 62753Notes

Reaction equation

[Cl:1][C:2]1[C:20]([O:21][CH:22]([CH3:24])[CH3:23])=[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:25][CH:26]([CH3:28])[CH3:27]>CO>[Cl:1][C:2]1[C:3]([O:25][CH:26]([CH3:27])[CH3:28])=[CH:4][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:19][C:20]=1[O:21][CH:22]([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 50 °C

Procedure

4-(4-Chloro-3,5-diisopropoxybenzamido)benzoic acid (AAA-112) (40 mg, 46%) was prepared from methyl 4-(4-chloro-3,5-diisopropoxybenzamido)benzoate (8) (86 mg, 0.21 mmol) using a procedure essentially the same as in step (ii) for AAA-001 except that MeOH was added dropwise to obtain a solution and the mixture was heated at 50° C. for 2 h then at RT for 15 h: m/z 390 [M−H]− (ES−), 1H NMR (400 MHz, DMSO-d6) δ: 12.74 (1H, br s), 10.44 (1H, s), 8.01-7.84 (4H, m), 7.29 (2H, s), 4.78 (2H, sep), 1.33 (12H, d).

Workup

additionwas added dropwise
customto obtain a solution

Sources & evidence

ORD record: ord-0a838db1dbc646bb9d65ecc31253d6a3
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447028B2

Reaction notes

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