Caprolactam → 6-(((Phenylmethoxy)carbonyl)amino)hexanoic acid

HRID 2407609Notes

Reaction equation

HRID 2407609 reaction equation
[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[OH-:20].[Na+]>>[CH2:13]([O:12][C:10]([NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:8])=[O:20])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 7768Caprolactam2×HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acid

Conditions

Temperature
7.5 °C

Procedure

5 g (44.2 mmol) of ε-caprolactam was dissolved in 19.4 g of 20 wt % NaOH and heated to reflux for 3-5 hours. After ε-caprolactam was hydrolyzed completely, the mixture was cooled down to 5-10° C. and 25 g of benzyl chloroformate was added. The mixture was stirred 1 hour at 5˜10° C. and then washed with 25 g of ethyl acetate twice. The pH of the aqueous layer was adjusted to 1-2 by adding 16% HCl and extracted with ethyl acetate twice. Combined ethyl acetate layer was washed with brine. The organic layer was dried by sodium sulfate and concentrated to obtain 6-benzyloxycarbonylamino-hexanoic acid. Purity was 95.0%.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3-5 hours
  3. washwashed with 25 g of ethyl acetate twice
  4. additionby adding 16% HCl
  5. extractionextracted with ethyl acetate twice
  6. washCombined ethyl acetate layer was washed with brine
  7. dry with materialThe organic layer was dried by sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cb99325df9b24c7980d1a1c9bb1a08dd
Source dataset
uspto-grants-2014_08
Patent number
US08809581B2

Reaction notes

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