Methyl 4-(3-chloro-4,5-bis(cyclopentyloxy)benzamido)benzoate → 4-(3-Chloro-4,5-bis(cyclopentyloxy)benzamido)benzoic acid

HRID 62732Notes

Reaction equation

HRID 62732 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([O:27][CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[C:20]=1[O:21][CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[C:5]([NH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1)=[O:6]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([O:27][CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[C:20]=1[O:21][CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1)=[O:6]

Participants

3

Reactant 1

HCID 67041663Methyl 4-(3-chloro-4,5-bis(cyclopentyloxy)benzamido)benzoate

Product 1

HCID 510338694-(3-Chloro-4,5-bis(cyclopentyloxy)benzamido)benzoic acidYield 77.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(3-Chloro-4,5-bis(cyclopentyloxy)benzamido)benzoic acid (AAA-044) (55 mg, 72%) was prepared from methyl 4-(3-chloro-4,5-bis(cyclopentyloxy)benzamido)benzoate (7) (75 mg, 0.16 mmol) using a procedure essentially the same as in Step (ii) for AAA-001, except that 1,4-dioxane (2.5 mL) was used instead of THF: m/z 442 [M−H]− (ES−); 1H NMR (400 MHz, DMSO-d6) δ: 12.74 (1H, br s), 10.45 (1H, s), 7.94 (2H, d), 7.88 (2H, d), 7.69 (1H, d), 7.52 (1H, d), 4.97 (2H, m), 1.99-1.93 (2H, m), 1.73-1.48 (14H, m).

Sources & evidence

ORD record
ord-445d7468f76843868895a1f1f82dd734
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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