Water → HCID 86710463, compound

HRID 2407607Notes

Reaction equation

HRID 2407607 reaction equation
[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH2:9].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])=[O:12]>[OH-].[Na+]>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][O:13][C:11]([NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:8])=[O:9])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 7768Caprolactam2×HCID 40723422-Chlorobenzyl chloroformate

Product 1

HCID 86710463HCID 86710463, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

1 g (8.8 mmol) of ε-caprolactam was dissolved in 3.88 g of 20 wt % NaOH solution and heated to reflux for 3-5 hours. After ε-caprolactam was hydrolyzed completely, the mixture was cooled down to 5˜10° C. and 5 g of water was added. 1.8 g (8.8 mmol) of 2-chlorobenzyl chloroformate was added dropwise. The mixture was stirred at room temperature for an hour and washed with 15 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-(2-Chloro-benzyloxycarbonylamino)-hexanoic acid. Purity was 98.9%.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3-5 hours
  3. temperaturethe mixture was cooled down to 5˜10° C.
  4. washwashed with 15 g of ethyl acetate twice
  5. additionby adding 16% HCl
  6. extractionextracted with ethyl acetate twice
  7. washCombined ethyl acetate layer was washed with brine
  8. dry with materialThe organic layer was dried by sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c03a6ea23e0741a3905f9c822f2d2676
Source dataset
uspto-grants-2014_08
Patent number
US08809581B2

Reaction notes

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