Hydrochloric Acid → Methyl 4'-({[(1-aminocyclopropyl)carbonyl]amino}methyl)-1,1'-biphenyl-2-carboxylate

HRID 10071Notes

Reaction equation

C(OC([NH:8][C:9]1([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:23]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:18][CH:17]=2)=[O:13])[CH2:11][CH2:10]1)=O)(C)(C)C.Cl>C(Cl)Cl.CO.C(Cl)(Cl)Cl>[NH2:8][C:9]1([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:23]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:18][CH:17]=2)=[O:13])[CH2:11][CH2:10]1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 4′-{[({1-[(tert-butoxycarbonyl)amino]cyclopropyl}carbonyl)-amino]methyl}-1,1′-biphenyl-2-carboxylate (0.84 g, 2.0 mmol) dissolved in a mixture of DCM (3 mL) and MeOH (45 mL) was cooled to 0° C. This homogenous solution was saturated with anhydrous hydrogen chloride and allowed to sit for 30 minutes. Dry nitrogen was then bubbled through the solution for about 30 min. Solvent was then removed under reduced pressure to yield an oily residue. The oil was then dissolved in DCM and the solvent removed. This process being repeated until a solid amine hydrochloride was obtained. Alternatively, the residue could be dissolved in chloroform followed by saturation with ammonia gas, filtration and solvent removal to obtain solid methyl 4′-({[(1-aminocyclopropyl)carbonyl]amino}methyl)-1,1′-biphenyl-2-carboxylate as the free-base.

Workup

customDry nitrogen was then bubbled through the solution for about 30 min
customSolvent was then removed under reduced pressure
customto yield an oily residue
customthe solvent removed
customwas obtained
filtrationfollowed by saturation with ammonia gas, filtration and solvent removal

Sources & evidence

ORD record: ord-efb62edd7ac24fc0b072a8bc9da1cb21
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091380B2

Reaction notes

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