Methyl 4-(3,4-di-tert-butoxy-5-chlorobenzamido)benzoate → 4-(3,4-Di-tert-butoxy-5-chlorobenzamido)benzoic acid

HRID 62738Notes

Reaction equation

HRID 62738 reaction equation
[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:22]=[C:23]([Cl:30])[C:24]=1[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:9]([NH:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1>[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:22]=[C:23]([Cl:30])[C:24]=1[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 67041868Methyl 4-(3,4-di-tert-butoxy-5-chlorobenzamido)benzoate

Product 1

HCID 510338734-(3,4-Di-tert-butoxy-5-chlorobenzamido)benzoic acidYield 65%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(3,4-Di-tert-butoxy-5-chlorobenzamido)benzoic acid (AAA-048) (110 mg, 64%) was prepared from methyl 4-(3,4-di-tert-butoxy-5-chlorobenzamido)benzoate (5) (175 mg, 0.403 mmol) using a procedure essentially the same as in Step (ii) for AAA-001, except that 1,4-dioxane (6 mL) was used instead of THF: m/z 418 [M−H]− (ES−); 1H NMR (400 MHz, DMSO-d6) δ: 12.78 (1H, br s). 10.49 (1H, s), 7.93 (2H, d), 7.87 (2H, d), 7.85 (1H, d), 7.59 (1H, d), 1.40 (9H, s), 1.34 (9H, s).

Sources & evidence

ORD record
ord-2a66b4c23e2241299310b90da27166b0
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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