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

HRID 1775989Notes

Reaction equation

HRID 1775989 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>[OH-].[Na+]>[CH2:14]([O:13][C:11]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 5646-Aminohexanoic AcidHCID 10387Benzyl chloroformate

Product 1

HCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acidYield 37.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
10 °C

Procedure

To a solution of 6-Amino hexanoic acid (50 grams, 379.65 mmol) in 1N Sodium hydroxide (95.3 ml) is cooled to 5 to 10° C. and simultaneously added from two separating funnels 4N Sodium hydroxide (190.6 ml) and Benzyl chloroformate (50% in Toluene, 196 grams) keeping the temperature at 5 to 10° C., later stirred at the same temperature for 2 hours and allowed to room temperature and stirred overnight. The reaction mixture is washed with Diisopropyl ether (3×200 ml), cooled to 10° C.; pH adjusted to 2 with dilute HCl, residue precipitated is filtered, dried and slurried in Diisopropyl ether to give pure 6-Benzyloxycarbonylamino hexanoic acid (38 grams) as white powder.

Workup

  1. customat 5 to 10° C.
  2. customallowed to room temperature
  3. stirringstirred overnight
  4. washThe reaction mixture is washed with Diisopropyl ether (3×200 ml)
  5. customprecipitated
  6. filtrationis filtered
  7. customdried

Sources & evidence

ORD record
ord-4468cd050d834c1fa4c994330fcc3435
Source dataset
uspto-grants-2016_02
Patent number
US09261626B2

Reaction notes

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