Water → HCID 51034083, compound

HRID 62742Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[C:24]([Cl:29])[C:25]=1[O:26][CH2:27][CH3:28])[C:5]([NH:7][C:8]1[CH:20]=[CH:19][C:11]([C:12]([O:14]C(C)(C)C)=[O:13])=[C:10]([O:21]C)[CH:9]=1)=[O:6].B(Cl)(Cl)Cl.O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[C:24]([Cl:29])[C:25]=1[O:26][CH2:27][CH3:28])[C:5]([NH:7][C:8]1[CH:20]=[CH:19][C:11]([C:12]([OH:14])=[O:13])=[C:10]([OH:21])[CH:9]=1)=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of tert-butyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methoxybenzoate (5) (55 mg, 0.13 mmol) in DCM (5 mL) was cooled to 0° C. and treated dropwise with a solution of 1 M boron trichloride in DCM (349 μL, 349 μmol). The reaction mixture was stirred at 0° C. for 1 h and then at RT for 2 h. The reaction mixture was cooled to 0° C. and water (0.5 mL) and sat. aq. NaHCO3 (2 mL) were added. The resulting white precipitate was collected by filtration and washed with water (2 mL). The solid was dried, then purified by capture and release on SAX, eluting with 5% AcOH in THF to afford 4-(3,5-dichloro-4-ethoxybenzamido)-2-hydroxybenzoic acid (AAA-057) (11 mg, 24%) as a white solid: m/z 370 [M+H]+ (ES+), 368 [M−H]− (ES−); 1H-NMR (400 MHz, DMSO-d6) δ: 10.51 (1H, s), 8.06 (2H, s), 7.76 (1H, d), 7.48 (1H, d), 7.28 (1H, dd), 4.14 (2H, q), 1.91 (1H, s), 1.40 (3H, t), 1.35 (1H, s).

Workup

waitat RT for 2 h
temperatureThe reaction mixture was cooled to 0° C.
filtrationThe resulting white precipitate was collected by filtration
washwashed with water (2 mL)
customThe solid was dried
custompurified by capture and release on SAX
washeluting with 5% AcOH in THF

Sources & evidence

ORD record: ord-a336d74826404518a0e0cd1b29e40c5c
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447028B2

Reaction notes

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