Hydrochloric Acid → Methyl 3-acetyl-5-(dipropylcarbamoyl)benzoate

HRID 1454185Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12](=[O:20])[N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH:21]([O:23]CCCC)=[CH2:22].C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:21]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12](=[O:20])[N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:23])[CH3:22]

Participants

Conditions

Temperature: 122 °C

Procedure

A mixture of methyl 3-bromo-5-(dipropylcarbamoyl)benzoate (342 mg, 1.0 mmol), 1-(vinyloxy)butane (200.4 mg, 0.26 mL, 2.0 mmol), palladium acetate (6.68 mg, 0.030 mmol), DPPP (27.2 mg, 0.066 mmol) and potassium carbonate (166 mg, 1.2 mmol) in DMF (2.5 mL) and H2O (0.3 mL) in a Smith process vial was heated at 122° C. in microwave for 3 h. The reaction mixture was cooled down to RT and hydrolyzed by addition of 5% HCl slowly. The reaction mixture was worked up by extraction with ethyl acetate and concentration under vacuum. The crude mixture was purified by reverse phase prep HPLC to give the title compound: HPLC retention time: 1.805 min (method A). MS (ESI) (M+H)+ 306.26.

Workup

extractionThe reaction mixture was worked up by extraction with ethyl acetate and concentration under vacuum
customThe crude mixture was purified by reverse phase prep HPLC

Sources & evidence

ORD record: ord-3c5ca06440cf4d33be52748d1a14560c
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07476764B2

Reaction notes

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