Ammonium formate → HCID 16005244, compound

HRID 2361000Notes

Reaction equation

[CH:1]([O-:3])=[O:2].[NH4+].[N:5]([C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][C@H:9]1[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N+]=[N-]>C(O)C.[Pd]>[C:14]([OH:16])(=[O:15])[C:1]([OH:3])=[O:2].[NH2:5][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][C@H:9]1[NH:19][C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21]

Participants

Conditions

Temperature: 50 °C

Procedure

7.5% Pd—C (100 mg) and ammonium formate (444.1 mg) were added at room temperature to a solution (10 mL) of ethyl (1S,3R,4S)-4-azido-3-[(t-butoxycarbonyl)amino]cyclohexanecarboxylate (1.0 g) in ethanol, followed by stirring at 50° C. for 1 hour. The catalyst was removed by filtration, and the filtrate was concentrated, to thereby yield 911.0 mg of crude ethyl (1S,3R,4S)-4-amino-3-t-butoxycarbonylaminocyclohexanecarboxylate. The crude product was dissolved in ethyl acetate (20 mL), and anhydrous oxalic acid (286.4 mg) was added to the solution, followed by stirring at room temperature for 16 hours. The formed crystals were recovered by filtration and dried, to thereby yield 1.16 g of the title compound.

Workup

customThe catalyst was removed by filtration
concentrationthe filtrate was concentrated
dissolutionThe crude product was dissolved in ethyl acetate (20 mL)
additionanhydrous oxalic acid (286.4 mg) was added to the solution
stirringby stirring at room temperature for 16 hours
filtrationThe formed crystals were recovered by filtration
customdried

Sources & evidence

ORD record: ord-7ce0b938470c4fc498971cce0d0ee968
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686189B2

Reaction notes

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