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

HRID 1049090
Notes
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Reaction equation

HRID 1049090 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 67396119Ethyl 4-{1-[(adamantan-1-ylcarbonyl)amino]-2-methylpropyl}benzoate

Product 1

HCID 58417123N-(1-{4-[(hydroxyamino)carbonyl]phenyl}-2-methylpropyl)adamantane-1-carboxamideYield 15%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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

  1. customThe reaction was capped
  2. temperatureAfter cooled to rt
  3. customThe solvent was then completely evaporated
  4. additionTo the solid was added DMSO (1.3 mL)
  5. filtrationThe solution was then filtered
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes