Hydrochloric Acid → 4-(((Benzyloxy)(hydroxy)methylidene)amino)cyclohexane-1-carboxylic acid

HRID 2361577Notes

Reaction equation

HRID 2361577 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].Cl.O>[OH-].[Na+]>[CH2:16]([O:15][C:13]([NH:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1)=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10387Benzyl chloroformateHCID 178479263HCID 178479263, compound

Product 1

HCID 2852474-(((Benzyloxy)(hydroxy)methylidene)amino)cyclohexane-1-carboxylic acidYield 84.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

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]30 =278, Rt=0.85 min (method 6)

Workup

  1. filtrationthe precipitate is filtered off
  2. customThe filter cake is dried

Sources & evidence

ORD record
ord-984512fce58a4640bbd84f20e44cd9dc
Source dataset
uspto-grants-2014_04
Patent number
US08691756B2

Reaction notes

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