Triethylamine → HCID 3008179, compound

HRID 1733659Notes

Reaction equation

HRID 1733659 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:24][O:25][C:26](=[O:33])[C@H:27]([C@H:29]([CH2:31][CH3:32])[CH3:30])[NH2:28].C(N(CC)CC)C.CS(ON1C2C=CC=CC=2N=N1)(=O)=O>ClCCl>[CH3:24][O:25][C:26](=[O:33])[C@H:27]([C@H:29]([CH2:31][CH3:32])[CH3:30])[NH:28][C:20](=[O:22])[C@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 11171351Isoleucine methyl ester hydrochlorideHCID 11745953Methanesulfonic acid, 1H-benzotriazol-1-yl ester

Product 1

HCID 3008179HCID 3008179, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Benzyloxycarbonyl-L-phenylalanine (3.0 g) and L-isoleucine methyl ester hydrochloride (1.82 g) are dissolved in anhydrous dichloromethane (30 ml), and thereto are added triethylamine (2.80 ml) and further 1-methanesulfonyloxy-1,2,3-benzotriazole (2.15 g) with stirring under ice-cooling, and the mixture is stirred at room temperature for 40 hours. After reaction, the solvent is distilled off and the resulting residue is extracted with ethyl acetate. The extract is washed with water, a saturated aqueous sodium hydrogen carbonate (5 times), water, 2 N hydrochloric acid and water in order and then dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off to give crystalline powder of N-(N-benzyloxycarbonyl-L-phenylalanyl)-L-isoleucine methyl ester (3.46 g), melting point: 94.5°-95.5° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at room temperature for 40 hours
  3. customAfter reaction
  4. distillationthe solvent is distilled off
  5. extractionthe resulting residue is extracted with ethyl acetate
  6. washThe extract is washed with water
  7. dry with materiala saturated aqueous sodium hydrogen carbonate (5 times), water, 2 N hydrochloric acid and water in order and then dried over anhydrous magnesium sulfate
  8. customAfter drying
  9. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-cc8358f437dd42b196889e85888aa3e4
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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