6-Aminohexanoic Acid → 6-(((Phenylmethoxy)carbonyl)amino)hexanoic acid

HRID 1678947Notes

Reaction equation

HRID 1678947 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[OH-].[Na+].[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCOCC>[CH2:12]([O:19][C:20]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 5646-Aminohexanoic AcidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×

Product 1

HCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acidYield 73.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 6-aminocaproic acid (13.1 g, 0.10 mole) in 2.5 N NaOH (40 ml, 0.10 mole) was cooled to 0° and benzyloxycarbonyl chloride (18.7 g, 0.11 mole) in ether (25 ml and 2.5N NaOH (50 ml, 0.125 mole) were added simultaneously in several portions, with vigorous stirring, over a 1 hr period. The reaction mixture was extracted with ether (3 × 50 ml), cooled in an ice-bath and acidified with 6M HCl. The crystalline product was recrystallized from ether-pet ether to give 19.4 g of product (73.2%); mp 54°-55.5°.

Workup

  1. extractionThe reaction mixture was extracted with ether (3 × 50 ml)
  2. temperaturecooled in an ice-bath
  3. customThe crystalline product was recrystallized from ether-pet ether

Sources & evidence

ORD record
ord-f29f4ccdcfa14294802bdbe7cbdf4978
Source dataset
uspto-grants-1978_03
Patent number
US04078049

Reaction notes

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