Water → HCID 3102539, compound

HRID 2407608Notes

Reaction equation

HRID 2407608 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][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:12]>[OH-].[Na+]>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([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])=[CH:16][CH:17]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 7768Caprolactam2×HCID 782054-Nitrobenzyl chloroformate

Product 1

HCID 3102539HCID 3102539, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
7.5 °C

Procedure

5 g (44.2 mmole) of ε-caprolactam was dissolved in 19.48 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 then 25 g of water and 10 g of 4-nitrobenzyl chloroformate were 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 water. The organic layer was dried by sodium sulfate and concentrated to obtain 6-(4-nitro-benzyloxycarbonylamino)-hexanoic acid. Purity was 93.9%.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3-5 hours
  3. temperaturethe mixture was cooled down to 5˜10° C.
  4. washwashed with 25 g of ethyl acetate twice
  5. additionby adding 16% HCl
  6. extractionextracted with ethyl acetate twice
  7. washCombined ethyl acetate layer was washed with water
  8. dry with materialThe organic layer was dried by sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b540da79fe3140c79903bf867ce95f79
Source dataset
uspto-grants-2014_08
Patent number
US08809581B2

Reaction notes

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