HCID 54098854, compound → HCID 22940392, compound

HRID 842642Notes

Reaction equation

HRID 842642 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C@H:10]2[CH2:12][C@H:11]2[C:13]([OH:15])=[O:14])[CH:7]=[CH:8][CH:9]=1)([O-])=O>C(O)C.O=[Pt]=O>[NH2:1][C:4]1[CH:5]=[C:6]([C@H:10]2[CH2:12][C@H:11]2[C:13]([OH:15])=[O:14])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 54098854HCID 54098854, compound

Product 1

HCID 22940392HCID 22940392, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

Cis-2-(3-nitrophenyl)cyclopropanecarboxylic acid (355 mg, 1.7 mmole), described in Example 21, was dissolved in 50 ml ethanol and 20 mg of PtO2 was added. Hydrogenation at atmospheric pressure for 1 hr. followed by filtration and evaporation of the solvent afforded 288 mg of cis-2-(3-aminophenyl)cyclopropanecarboxylic acid. 177 mg (1 mmole) of cis-2-(3-aminophenyl)cyclo-propanecarboxylic acid was dissolved in water (1 mL), t-BuOH (1 mL) and 2M NaOH (0.5 mL, 1 mmole). 250 μL (1.1 mmole) of di-tert-butyl dicarbonate was then added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into ice and water and acidified with dilute H2SO4 and extracted with dichloromethane affording 264 mg of pure BOC protected cis-2-(3-aminophenyl)-cyclopropanecarboxylic acid. This acid was transformed to BOC protected title compound according to the Procedure in Example 7. Finally, deprotection with THF 1 and 6M HCl 1 gave the title product. Analysis: Calculated: C 59.5, H. 5.0, N 18.5.

Workup

  1. filtrationfollowed by filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-f01934d987f743cdb46b4293307a3291
Source dataset
uspto-grants-2002_04
Patent number
US06376492B1

Reaction notes

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