Triethylamine → HCID 53791264, compound

HRID 1733658Notes

Reaction equation

HRID 1733658 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:20]([O:22][C:23](=[O:29])[C@H:24]([CH:26]([CH3:28])[CH3:27])[NH2:25])[CH3:21].C(N(CC)CC)C.CS(ON1C2C=CC=CC=2N=N1)(=O)=O>ClCCl.C(OCC)(=O)C.O>[CH2:20]([O:22][C:23](=[O:29])[C@H:24]([CH:26]([CH3:28])[CH3:27])[NH:25][C:16](=[O:18])[C@H:12]([CH:13]([CH3:14])[CH3:15])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH3:21]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 87181Ethyl L-valinate hydrochlorideHCID 726987N-Carbobenzoxy-L-valineHCID 11745953Methanesulfonic acid, 1H-benzotriazol-1-yl ester

Product 1

HCID 53791264HCID 53791264, compoundYield 90.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Benzyloxycarbonyl-L-valine (1.25 g) and L-valine ethyl ester hydrochloride (1.08 g) are dissolved in dichloromethane (15 ml) and thereto are added triethylamine (1.54 ml) and further 1-methanesulfonyloxy-1,2,3-benzotriazole (1.07 g) under ice-cooling. After allowing to stand at room temperature for 72 hours, to the reaction mixture are added water and ethyl acetate. The ethyl acetate layer is separated, washed with water, dried and then the solvent is distilled off to give N-(N-benzyloxycarbonyl-L-valyl)-L-valine ethyl ester (1.70 g). The product is washed with petroleum ether to give powdery product (1.50 g), melting point: 93°-93.5° C.

Workup

  1. temperaturecooling
  2. customThe ethyl acetate layer is separated
  3. washwashed with water
  4. customdried
  5. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-17cc5afabcf343908833d02695e8372c
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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