Dichloromethane → N-(1-methylcyclobutyloxycarbonyl) phenylalanine alanine methyl ester

HRID 1605185Notes

Reaction equation

HRID 1605185 reaction equation
[CH3:1][C:2]1([O:6][C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:8])[CH2:5][CH2:4][CH2:3]1.Cl.[CH3:22][O:23][C:24](=[O:28])[C@H:25]([CH3:27])[NH2:26].C(Cl)Cl>C(N(CC)CC)C>[CH3:1][C:2]1([O:6][C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:8])[CH2:3][CH2:4][CH2:5]1.[CH3:22][O:23][C:24](=[O:28])[C@H:25]([CH3:27])[NH2:26]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2733257Alanine methyl ester hydrochlorideHCID 53813823N-(1-methylcyclobutyloxycarbonyl) phenylalanine

Product 1

HCID 68136398N-(1-methylcyclobutyloxycarbonyl) phenylalanine alanine methyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 0.67 mM of the hydroxysuccinimide ester of N-(1-methylcyclobutyloxycarbonyl) phenylalanine and 0.70 mM of alanine methyl ester hydrochloride in 10 ml. of methylene chloride is treated with triethylamine until the pH is adjusted to 7.6-8.0. Reaction is stirred 6 hours and the reaction mixture is washed according to the following procedure: one time with dilute sodium bicarbonate solution; once with 50% saturated sodium chloride solution; once with 0.2 N sulfuric acid saturated with sodium sulfate; and two times with 50% saturated sodium chloride solution. The resulting material is dried over sodium sulfate and the washing procedure repeated. The solvent is removed in vacuo to afford N-(1-methylcyclobutyloxycarbonyl) phenylalanine-alanine methyl ester.

Workup

  1. customReaction
  2. washthe reaction mixture is washed
  3. dry with materialThe resulting material is dried over sodium sulfate
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-f1d423cee15f4e7cbaa3c8805c522a4a
Source dataset
uspto-grants-1976_04
Patent number
US03948971

Reaction notes

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