Triethylamine → HCID 68137264, compound

HRID 1605186Notes

Reaction equation

HRID 1605186 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].[CH2:15](N(CC)CC)C.Cl[C:23]([O:25][C:26]1(C)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:24]>C(Cl)(Cl)Cl>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1([CH3:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH2:9]1)[NH:6][C:23]([O:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:24]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 21549113HCID 21549113, compound

Product 1

HCID 68137264HCID 68137264, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A suspension of 0.59 g. (2.1 mM) of phenylalanine methylester hydrochloride in 10 ml. of chloroform is cooled to 0°C. After the pH of the mixture is adjusted to 8 by addition of triethylamine, 4.5 mM of 1-methylcyclohexyl chloroformate is added portion-wise at 0°C. while maintaining the pH of the reaction at 8 by addition of triethylamine. The reaction is stirred overnight at 20°-25°C. After adding chloroform, the reaction mixture is washed with 5% sodium bicarbonate solution, 50% saturated sodium chloride solution, 0.2 N sulfuric acid saturated with sodium sulfate, twice with 50% saturated sodium chloride solution, and then the reaction solution is dried over sodium sulfate. The solvent is removed to afford an oil of 1-methylcyclohexyloxycarbonyl phenylalanine methyl ester.

Workup

  1. additionA suspension of 0.59 g
  2. additionis added portion-wise at 0°C.
  3. temperaturewhile maintaining
  4. customthe pH of the reaction at 8
  5. washthe reaction mixture is washed with 5% sodium bicarbonate solution, 50% saturated sodium chloride solution, 0.2 N sulfuric acid saturated with sodium sulfate, twice with 50% saturated sodium chloride solution
  6. dry with materialthe reaction solution is dried over sodium sulfate
  7. customThe solvent is removed

Sources & evidence

ORD record
ord-1a410f54ec95429d9874a65cb91a4777
Source dataset
uspto-grants-1976_04
Patent number
US03948971

Reaction notes

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