Benzyl chloroformate → HCID 178523389, compound

HRID 263433Notes

Reaction equation

HRID 263433 reaction equation
[NH2:1][CH2:2][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]>[OH-].[Na+]>[C:13]([NH:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]1)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 178511262HCID 178511262, compound

Product 1

HCID 178523389HCID 178523389, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a 0° C. solution of trans-4-aminomethyl-1-cyclohexane carboxylic acid (6.28 g, 0.04 mol) in 10% aqueous NaOH (16 mL) was added dropwise benzyl chloroformate (8.29 g, 0.049 mol) and 10% aqueous NaOH (20 mL). The cold bath was removed and the reaction mixture was stirred vigorously for one hour. The thick white paste was shaken with aqueous 1M HCl (100 mL) and the white solid was isolated by filtration, washed with H2O, and dried overnight in vacuo to give trans-4-(N-carbobenzyloxy)aminomethyl-1-cyclohexane carboxylic acid.

Workup

  1. customThe cold bath was removed
  2. stirringThe thick white paste was shaken with aqueous 1M HCl (100 mL)
  3. customthe white solid was isolated by filtration
  4. washwashed with H2O
  5. customdried overnight in vacuo

Sources & evidence

ORD record
ord-27862573d0c1454e82d45f951d147c8d
Source dataset
uspto-grants-1997_07
Patent number
US05643922

Reaction notes

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