Triethylamine → HCID 70591612, compound

HRID 1733660Notes

Reaction equation

HRID 1733660 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.[ClH:19].[CH2:20]([O:22][C:23](=[O:26])[CH2:24][NH2:25])[CH3:21].C(N(CC)CC)C.CS(ON1C2C=CC=CC=2N=N1)(=O)=O>C(Cl)(Cl)Cl.C(OCC)(=O)C.O>[ClH:19].[CH2:20]([O:22][C:23](=[O:26])[CH2:24][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 726987N-Carbobenzoxy-L-valineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 11745953Methanesulfonic acid, 1H-benzotriazol-1-yl ester

Product 1

HCID 70591612HCID 70591612, compoundYield 58.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Benzyloxycarbonyl-L-valine (1.26 g), glycine ethyl ester hydrochloride (0.70 g) and triethylamine (1.40 ml) are dissolved in anhydrous chloroform (10 ml), and thereto is added 1-methanesulfonyloxy-1,2,3-benzotriazole (1.05 g) with stirring under ice-cooling. After stirrig at room temperature for 20 hours, to the reaction mixture are added water and ethyl acetate. The ethyl acetate layer is separated, washed and dried. After drying, the solvent is distilled off to give N-(N-benzyloxycarbonyl-L-valyl)glycine ethyl ester hydrochloride (1.1 g), melting point: 162°-165° C.

Workup

  1. temperaturecooling
  2. customThe ethyl acetate layer is separated
  3. washwashed
  4. customdried
  5. customAfter drying
  6. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-8f6f15c0d46a441da51fbe7d11fe13c1
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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