1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 131724651, compound

HRID 2416125Notes

Reaction equation

HRID 2416125 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:23]([CH3:32])[C@H:24]([C:28]([O:30][CH3:31])=[O:29])[CH:25]([CH3:27])[CH3:26].Cl.C(N(C(C)C)CC)(C)C.CCN=C=NCCCN(C)C>ClCCl>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@@H:2]([C:10]([N:23]([CH3:32])[C@H:24]([C:28]([O:30][CH3:31])=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 675678N-(Benzyloxycarbonyl)-D-phenylalanineHCID 13819431HCID 13819431, compound

Product 1

HCID 131724651HCID 131724651, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 16.1 g of Z-DPhe-OH, 10 g of H-NMeVal-OMe hydrochloride and 10.1 ml of diisopropyl-ethylamine in 100 ml of dichloromethane is cooled to 0-5° and 11.35 g of EDCI are added. The mixture is first stirred-for one hour at 0-5°, then overnight at room temperature. The solvent is removed and the residue is taken up in MTBE and washed with Na2CO3 (5%), 1N HCl and water and dried. After removal of the solvent, Z-DPhe-NMeVal-OMe is obtained in a yield of 84.5%.

Workup

  1. customovernight
  2. customat room temperature
  3. customThe solvent is removed
  4. washwashed with Na2CO3 (5%), 1N HCl and water
  5. customdried
  6. customAfter removal of the solvent

Sources & evidence

ORD record
ord-762850ea019c4e6c9f0853d505490397
Source dataset
uspto-grants-2004_11
Patent number
US06822074B1

Reaction notes

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