Triethylamine → 3-(1-Carboxycyclopentyl)-2-aminopropanoic acid t-butyl ester

HRID 1087974Notes

Reaction equation

HRID 1087974 reaction equation
Cl.[C:2]([O:6][C:7](=[O:34])[CH:8](CN(CC1C=CC=CC=1)CC1C=CC=CC=1)[CH2:9][C:10]1([C:15]([OH:17])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1)([CH3:5])([CH3:4])[CH3:3].C([N:37](CC)CC)C>C(O)C.[Pd]>[C:2]([O:6][C:7](=[O:34])[CH:8]([NH2:37])[CH2:9][C:10]1([C:15]([OH:17])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 700475663-(1-Carboxycyclopentyl)-2-(dibenzylaminomethyl)propanoic acid t-butyl ester hydrochloride

Product 1

HCID 543524343-(1-Carboxycyclopentyl)-2-aminopropanoic acid t-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(1-Carboxycyclopentyl)-2-(dibenzylaminomethyl)propanoic acid t-butyl ester hydrochloride (20.0 g; 41 mmol) in ethanol (160 ml) and triethylamine (2.0 ml) was hydrogenated over palladium (from 20% Pd(OH)2 /C; 20 g) at 60 p.s.i. (4.1 bar). After eighteen hours the mixture was filtered through arbicel, the solvent evaporated and the residue dried azeotropically with toluene. The required primary amino acid triethylamine salt, containing one mole equivalent of triethylamine hydrochloride was thus obtained as a white solid (16.21 g).

Workup

  1. filtrationAfter eighteen hours the mixture was filtered through arbicel
  2. customthe solvent evaporated
  3. dry with materialthe residue dried azeotropically with toluene
  4. additionThe required primary amino acid triethylamine salt, containing one mole equivalent of triethylamine hydrochloride

Sources & evidence

ORD record
ord-0fa2c1cde6e246bfb9d368795db5fcb7
Source dataset
uspto-grants-1990_10
Patent number
US04960792

Reaction notes

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