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

HRID 444709

Reaction equation

HRID 444709 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]+=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-7fa5e7f5d2b04f0db1b9df18ae18187f
Source dataset
uspto-grants-2013_07
Patent number
US08476224B2

Linked notes

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