Réaction #531891

ord-7fa5e7f5d2b04f0db1b9df18ae18187f

Équation de réaction

O
H2O
Cl
HCl
Cl.N[C@H]1CC[C@H](C(=O)O)CC1
trans-4-aminocyclohexane carboxylic acid hydrochloride
O=C(Cl)OCc1ccccc1
benzyl chloroformate
→
O=C(NC1CCC(C(=O)O)CC1)OCc1ccccc1
4-benzyloxycarbonylamino-cyclohexanecarboxylic acid
Rendement 84.7%

Réactifs

O
H2O
Cl
HCl
Cl.N[C@H]1CC[C@H](C(=O)O)CC1
trans-4-aminocyclohexane carboxylic acid hydrochloride
O=C(Cl)OCc1ccccc1
benzyl chloroformate

Réactifs

Aucun

Solvants

[Na+].[OH-]
NaOH

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Filtrationthe precipitate is filtered off
  2. 2
    AutreThe filter cake is dried

Mode opératoire

To a solution of trans-4-aminocyclohexane carboxylic acid hydrochloride (5.0 g, 34.92 mmol) in aqueous 2.0N NaOH (35 mL) is added benzyl chloroformate (5.0 mL, 34.92 mmol). The mixture stirs for 1.5 h. Then the suspension is acidified with 12N HCl (aq) to pH=1. H2O is added (100 mL) and the precipitate is filtered off. The filter cake is dried to afford 8.2 g of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid. LC/MS: [M+H]+=278, Rt=0.85 min (method 6)

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08476224B2uspto-grants-2013_07