Methyl 4-aminobenzoate → Methyl 4-(3,4-di-tert-butoxy-5-chlorobenzamido)benzoate

HRID 62737Notes

Reaction equation

[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([Cl:20])[C:14]=1[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:9](O)=[O:10])([CH3:4])([CH3:3])[CH3:2].[NH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>>[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([Cl:20])[C:14]=1[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:9]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 12082Methyl 4-aminobenzoate

HCID 81531Diisopropylethylamine

HCID 670417783,4-Di-tert-butoxy-5-chlorobenzoic acid

Product 1

HCID 67041868Methyl 4-(3,4-di-tert-butoxy-5-chlorobenzamido)benzoateYield 50%

Procedure

Methyl 4-(3,4-di-tert-butoxy-5-chlorobenzamido)benzoate (5) (185 mg, 50%) was prepared from 3,4-di-tert-butoxy-5-chlorobenzoic acid (3) (250 mg, 0.831 mmol) using a procedure essentially the same as in Step (i) for AAA-019 except that methyl 4-aminobenzoate was used instead of methyl 4-amino-2-methylenzoate and TEA (579 μL, 4.16 mmol) was used as base instead of DIPEA: m/z 432 [M−H]− (ES−); 1H NMR (400 MHz, DMSO-d6) δ: 10.54 (1H, s), 7.96 (2H, d), 7.91 (2H, d), 7.86 (1H, d), 7.60 (1H, d), 3.84 (3H, s), 1.41 (9H, s), 1.32 (9H, s).

Sources & evidence

ORD record: ord-3c93c3017995443f8516fa6f604ec1ea
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447028B2

Reaction notes

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