Methanol → N-(1-{4-[(hydroxyamino)carbonyl]phenyl}-2-methylpropyl)adamantane-1-carboxamide

HRID 1049090Notes

Reaction equation

[C:1]12([C:11]([NH:13][CH:14]([C:18]3[CH:28]=[CH:27][C:21]([C:22]([O:24]CC)=O)=[CH:20][CH:19]=3)[CH:15]([CH3:17])[CH3:16])=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH-:29].[K+].Cl.[NH2:32]O.CO>C(O)(=O)C>[OH:29][NH:32][C:22]([C:21]1[CH:20]=[CH:19][C:18]([CH:14]([NH:13][C:11]([C:1]23[CH2:10][CH:5]4[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]4)[CH2:8]2)[CH2:2]3)=[O:12])[CH:15]([CH3:16])[CH3:17])=[CH:28][CH:27]=1)=[O:24]

Participants

Conditions

Temperature: 80 °C

Procedure

To the crude ethyl 4-{1-[(adamantan-1-ylcarbonyl)amino]-2-methylpropyl}benzoate in a vial was added potassium hydroxide (0.11 g, 1.87 mmol), hydroxylamine hydrochloride (0.047 g, 0.68 mmol), and methanol (2 mL). The reaction was capped and heated at 80° C. for 1 h. After cooled to rt, acetic acid (0.097 mL, 1.7 mmol was added to neutralize the excess base. The solvent was then completely evaporated. To the solid was added DMSO (1.3 mL). The solution was then filtered and purified by prep-HPLC purification to give the title compound (0.009 g, 15%) as a white solid. LC-MS: (FA) ES+ 371.

Workup

customThe reaction was capped
temperatureAfter cooled to rt
customThe solvent was then completely evaporated
additionTo the solid was added DMSO (1.3 mL)
filtrationThe solution was then filtered
custompurified by prep-HPLC purification

Sources & evidence

ORD record: ord-49d042249e7a4cf19e355bae2fadd751
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382197B2

Reaction notes

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