1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → BOC-Leu-Gly-OBzl

HRID 2083815Notes

Reaction equation

HRID 2083815 reaction equation
CCN=C=NCCCN(C)C.[NH:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:13]([C:18]([OH:20])=O)[CH2:14][CH:15]([CH3:17])[CH3:16].CC1C=CC(S(O)(=O)=O)=CC=1.[CH:39]1[CH:44]=[CH:43][C:42]([CH2:45][O:46][C:47]([CH2:49][NH2:50])=[O:48])=[CH:41][CH:40]=1>ClCCl.CN(C=O)C.C1C=CC2N(O)N=NC=2C=1>[NH:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:13]([C:18]([NH:50][CH2:49][C:47]([O:46][CH2:45][C:42]1[CH:43]=[CH:44][CH:39]=[CH:40][CH:41]=1)=[O:48])=[O:20])[CH2:14][CH:15]([CH3:16])[CH3:17]

Participants

7

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 6451311O-benzylglycine toluene-p-sulphonate

Product 1

HCID 13242213BOC-Leu-Gly-OBzlYield 108.5%

Reagents, catalysts & solvents 3

HCID 757711-HydroxybenzotriazoleCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

A solution of WSC (34 g.) in dichloromethane (50 ml.) was added dropwise to a suspension of BOC-Leu-OH (46.2 g.), HOBT (1 g.) and H-Gly-OBzl.TosOH (74 g.) in DMF (100 ml.) and dichloromethane (200 ml.) with stirring at -5° C. for 1 hour. After 1 hour, the solution was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo to remove dichloromethane. To the DMF layer was added water and the mixture was extracted with ethyl acetate (1 l.), and again with the same solvent (500 ml.). The ethyl acetate layer was washed with 1 N HCl, water, 5% sodium bicarbonate and water, in this order and dehydrated with sodium sulfate (anhydrous), then concentrated in vacuo to obtain oily BOC-Leu-Gly-OBzl (82 g.) Rf = 0.68.

Workup

  1. waitAfter 1 hour
  2. stirringthe solution was stirred overnight at room temperature
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto remove dichloromethane
  5. additionTo the DMF layer was added water
  6. extractionthe mixture was extracted with ethyl acetate (1 l.)
  7. washThe ethyl acetate layer was washed with 1 N HCl, water, 5% sodium bicarbonate and water, in this order
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e276ec86b51a4806a99a70c32a84534e
Source dataset
uspto-grants-1978_04
Patent number
US04086221

Reaction notes

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