1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67675259, compound

HRID 1956971Notes

Reaction equation

HRID 1956971 reaction equation
[C:1]([N:8]([CH3:20])[C@@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH3:22][O:23][C:24](=[O:37])[C@H:25]([CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)[NH2:26].OC1C2N=NNC=2C=CC=1.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[CH3:22][O:23][C:24](=[O:37])[C@H:25]([CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)[NH:26][C:17](=[O:19])[C@@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH3:20]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2734891Methyl tryptophanate hydrochlorideHCID 7015127N-Boc-N-methyl-D-phenylalanineHCID 178418300HCID 178418300, compound

Product 1

HCID 67675259HCID 67675259, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-BOC-N-methyl-(D)-phenylalanine (2.1 g, 7.5 mmol) [BOC=tert-butyloxycarbonyl] in dry DMF [N,N-dimethylformamide] (15 ml) are added (L)-tryptophan methyl ester hydrochloride (2 g, 7.8 mmol) and hydroxybenztriazole (1.2 g, 8.8 mmol). The mixture is cooled to 0° and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.7 ml, 9.2 mmol) is added dropwise. The reaction mixture is slowly warmed to r.t. (room temperature) and stirring continued for 2 hours. The homogeneous mixture is diluted with ethyl acetate (500 ml) and washed with three portions of water (200 ml). The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo to give N-BOC-N-methyl-(D)-phenylalanyl-(L)-tryptophan methyl ester as a white foam. [a]D =+42° (c=1.0, ethanol).

Workup

  1. temperatureThe mixture is cooled to 0°
  2. washwashed with three portions of water (200 ml)
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26c214596520483a95dfbaa2ec4e52d0
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

Loading…