Hydrochloric Acid → HCID 10545489, compound

HRID 2256833Notes

Reaction equation

HRID 2256833 reaction equation
[C:1]([CH2:4][C@@H:5]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])([OH:3])=O.[CH:20]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.Cl>C(Cl)Cl>[CH:20]1([NH:26][C:1]([CH2:4][C@@H:5]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[O:3])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7965CyclohexylamineHCID 22874407HCID 22874407, compound

Product 1

HCID 10545489HCID 10545489, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl (2R)-2-carboxymethyl-4-methylvalerate (527 mg) and cyclohexylamine (238 mg) in methylene chloride (10 ml) was added WSCD.HCl (460 mg) at room temperature. After being stirred overnight, the mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (30 ml). The solution was washed with 5% HCl, water, saturated sodium bicarbonate and water, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with n-hexane to give benzyl (2R)-2-(cyclohexylcarbamoylmethyl)-4-methylvalerate (410 mg).

Workup

  1. customat room temperature
  2. concentrationthe mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate (30 ml)
  4. washThe solution was washed with 5% HCl, water, saturated sodium bicarbonate and water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-304a4c1403954215b8033d23903529fc
Source dataset
uspto-grants-1997_08
Patent number
US05656604

Reaction notes

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