Maleic Acid → HCID 67899375, compound

HRID 1030509Notes

Reaction equation

HRID 1030509 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH:9]1([C:12]2[N:16]=[C:15]([C@@H:17]3[C@@H:22]4[CH2:23][N:19]([CH2:20][CH2:21]4)[CH2:18]3)[O:14][N:13]=2)[CH2:11][CH2:10]1>CO.C(OCC)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH:9]1([C:12]2[N:16]=[C:15]([C@@H:17]3[C@@H:22]4[CH2:23][N:19]([CH2:20][CH2:21]4)[CH2:18]3)[O:14][N:13]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 444266Maleic AcidHCID 10921655HCID 10921655, compound

Product 1

HCID 67899375HCID 67899375, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of anhydrous maleic acid (4.30 g, 0.037 mol) in methanol (12 mL) and diethyl ether (4 mL) was added to a filtered solution of (3R,4R)-3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-azabicyclo[2.2.1]heptane free base (7.60 g, 0.037 mol) in methanol (6 mL) and diethyl ether (6 mL). After ageing at 5° C. for 16 hours the hydrogen maleate salt (9.10 g) was collected, mp 126° C. (propan-2-ol). [α]21D°C. -7.0° (c=1.0, CH2Cl2). (Found: C, 56.06; H, 5.97; N, 13.04. C11H15N3O. C4H4O4 requires C, 56.07; H, 5.96; N, 13,08%).

Workup

  1. customthe hydrogen maleate salt (9.10 g) was collected
  2. custom-7.0° (c=1.0, CH2Cl2)

Sources & evidence

ORD record
ord-b9e9912a74f04e66a40d1527eaa5eb19
Source dataset
uspto-grants-1992_04
Patent number
US05106853

Reaction notes

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