Cyclohexylamine → HCID 18187647, compound

HRID 127622Notes

Reaction equation

HRID 127622 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].Br[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>C(O)C>[C:18]([O:17][C:15](=[O:16])[CH2:14][NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 79177tert-Butyl bromoacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 18187647HCID 18187647, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of cyclohexylamine (61.0 g, 0.615 mol) and sodium bicarbonate (12.9 g, 0.154 mol) in 200 ml of ethanol was added dropwise t-butyl bromoacetate (30.0 g, 0.154 mol). After 72 hours the ethanol was evaporated and the residue partitioned between water and chloroform. The chloroform layer was washed with water, dried, filtered and concentrated under vacuum to give 31.9 g (97%) of N-cyclohexylglycine t-butyl ester as an oil, Rf =0.59 (25% acetone/25% ethyl acetate/50% hexane).

Workup

  1. customAfter 72 hours the ethanol was evaporated
  2. customthe residue partitioned between water and chloroform
  3. washThe chloroform layer was washed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0af5f4fb083f4f57ae94a0ec9b92207e
Source dataset
uspto-grants-1981_03
Patent number
US04256761

Reaction notes

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