Galactaric acid → HCID 131723925, compound

HRID 1369458Notes

Reaction equation

[O:1]=[C:2]([OH:14])[C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([C:11]([OH:13])=[O:12])[OH:10])[OH:8])[OH:6])[OH:4].[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][C:22]23[NH:28][CH:25]([CH2:26][CH2:27]2)[CH2:24][CH2:23]3)[CH:16]=1>CO.O>[O:1]=[C:2]([OH:14])[C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([C:11]([OH:13])=[O:12])[OH:10])[OH:8])[OH:6])[OH:4].[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][C:22]23[NH:28][CH:25]([CH2:26][CH2:27]2)[CH2:24][CH2:23]3)[CH:16]=1.[N:15]1[CH:16]=[CH:17][CH:18]=[C:3]([CH2:5][C:7]23[NH:15][CH:16]([CH2:17][CH2:18]2)[CH2:11][CH2:9]3)[CH:2]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of galactaric acid (19 mg, 0.09 mmol) in methanol (2 mL) was added to 2-((3-pyridylmethyl)-7-azabicyclo[2.2.1]heptane (34 mg, 0.18 mmol). Three drops of water were added and the mixture was heated to 50° C. followed by sonication. This produced a clear solution, which was filtered through a glass wool plug while still warm. The plug was washed with hot methanol and the combined filtrates were rotary evaporated to reveal a solid. This was recrystallized from ethanol to give 2-((3-pyridylmethyl)-7-azabicyclo[2.2.1]heptane hemigalactarate (30 mg, 57%), as a cream colored powder (mp 189-193° C.).

Workup

customfollowed by sonication
customThis produced a clear solution, which
filtrationwas filtered through a glass wool plug
temperaturewhile still warm
washThe plug was washed with hot methanol
customthe combined filtrates were rotary evaporated
customThis was recrystallized from ethanol

Sources & evidence

ORD record: ord-9d623ad8f53d40c4b4411d34c3cef232
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06579878B1

Reaction notes

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