Hydrochloric Acid → {[4-(Adamantan-1-yl)phenyl]amino}(oxo)acetic acid

HRID 1626773Notes

Reaction equation

C1COCC1.[C:6]12([C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:29])[C:24]([O:26]CC)=[O:25])=[CH:18][CH:17]=3)[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2.[OH-].[Na+].Cl>C(O)C>[C:6]12([C:16]3[CH:17]=[CH:18][C:19]([NH:22][C:23](=[O:29])[C:24]([OH:26])=[O:25])=[CH:20][CH:21]=3)[CH2:7][CH:8]3[CH2:9][CH:10]([CH2:11][CH:12]([CH2:14]3)[CH2:13]1)[CH2:15]2

Participants

Conditions

Temperature: 70 °C

Procedure

THF (18 mL) and ethanol (6 mL) were added to 600 mg (1.83 mmol) of ethyl {[4-(adamantan-1-yl)phenyl]amino}(oxo)acetate. Thereafter, 2.7 mL of 1N aqueous sodium hydroxide solution was added, and the mixture was heated at 70° C. for 2 hours. Next, 1N hydrochloric acid was added to acidify the mixture, and the organic solvent was distilled off under reduced pressure. The resulting solids were filtered and washed with H2O and n-hexane, followed by drying, thereby giving 492 mg of {[4-(adamantan-1-yl)phenyl]amino}(oxo)acetic acid (yield: 90%).

Workup

distillationthe organic solvent was distilled off under reduced pressure
filtrationThe resulting solids were filtered
washwashed with H2O and n-hexane
customby drying

Sources & evidence

ORD record: ord-78912d8daaba418c96f03adb69966def
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785473B2

Reaction notes

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