1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → BOC-Tyr(Bzl)-Pro-OBzl

HRID 256494

Reaction equation

HRID 256494 reaction equation
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([OH:20])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[NH:28]1[CH2:42][CH2:41][CH2:40][C@H:29]1[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31].Cl.CCN=C=NCCCN(C)C>ClCCl>[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([N:28]1[CH2:42][CH2:41][CH2:40][C@H:29]1[C:30]([O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:31])=[O:20])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 2733413Proline benzyl ester hydrochloride

Product 1

HCID 131715373BOC-Tyr(Bzl)-Pro-OBzlYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 10.00 g of BOC-Tyr(Bzl)-OH dissolved in 50 ml of dichloromethane was mixed with 6.53 g of H-Pro-OBzl.HCl. To this mixture, under cooling at -5° C., 4.93 ml of WSC was added, followed by stirring at -5° C. for one hour and at room temperature overnight. The reaction mixture was concentrated under reduced pressure, the residue was mixed by shaking with ethyl acetate and 1N hydrochloric acid and separated into liquid layers. The ethyl acetate layer was washed successively twice with 1N hydrochloric acid, twice with saturated aqueous sodium chloride, three times with 5% aqueous sodium hydrogen carbonate and twice with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 14.46 g (yield: 96.1%) of BOC-Tyr(Bzl)-Pro-OBzl as oily product. Rf1 =0.71.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was mixed
  3. stirringby shaking with ethyl acetate and 1N hydrochloric acid
  4. customseparated into liquid layers
  5. washThe ethyl acetate layer was washed successively twice with 1N hydrochloric acid, twice with saturated aqueous sodium chloride, three times with 5% aqueous sodium hydrogen carbonate and twice with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e1afc80ba44c4e7496a5518c27e63786
Source dataset
uspto-grants-1987_10
Patent number
US04703106

Linked notes

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