Dicyclohexylcarbodiimide → Methyl bis-(3,4-methylenedioxyphenylmethyl)acetyl-(alpha-methyl-D-tryptophan)

HRID 976042Notes

Reaction equation

HRID 976042 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH:11]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]4[O:22][CH2:23][O:24][C:18]=4[CH:17]=3)[C:12](O)=O)=[CH:4][C:3]=2[O:2]1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N([OH:49])N=NC=2C=1.[CH3:50][NH:51][C@@:52]([CH3:66])([C:63]([OH:65])=[O:64])[CH2:53][C:54]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[NH:56][CH:55]=1>CN(C=O)C.CCOC(C)=O>[CH3:12][C:11]([CH2:10][C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)([CH2:15][C:16]1[CH:21]=[CH:20][C:19]2[O:22][CH2:23][O:24][C:18]=2[CH:17]=1)[C:50]([NH:51][C@@:52]([CH3:66])([C:63]([OH:65])=[O:64])[CH2:53][C:54]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[NH:56][CH:55]=1)=[O:49]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 19968575Bis-(3,4-methylenedioxyphenylmethyl)acetic acidHCID 86750506methyl alpha-methyl-D-tryptophan

Product 1

HCID 86750507Methyl bis-(3,4-methylenedioxyphenylmethyl)acetyl-(alpha-methyl-D-tryptophan)Yield 48.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.0 g (3.0 mmol) of bis-(3,4-methylenedioxyphenylmethyl)acetic acid in 20 mL DMF was treated with 0.68 g (3.3 mmol) of DCC and 0.45 g (3.3 mmol) of HOBt. A solution of 0.73 g (3.15 mmol) of methyl α-methyl-D-tryptophan in 20 mL EtOAc was then added and the solution left stirring for 3 days. The mixture was filtered and the solvent removed under reduced pressure. The residue was taken up in EtOAc and washed with 1N HCl, then saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left the crude product. Chromatography on silica gel, eluting with a gradient of 10% EtOAc in hexane to 50% EtOAc in hexane gave 0.78 g (48.8% yield) of the product as a white foam. The structure was confirmed by NMR spectroscopy.

Workup

  1. waitthe solution left
  2. filtrationThe mixture was filtered
  3. customthe solvent removed under reduced pressure
  4. washwashed with 1N HCl
  5. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  6. waitleft the crude product
  7. washChromatography on silica gel, eluting with a gradient of 10% EtOAc in hexane to 50% EtOAc in hexane

Sources & evidence

ORD record
ord-3f4e2abb31fa446cb02fa0fb735f43af
Source dataset
uspto-grants-1997_03
Patent number
US05610177

Reaction notes

Loading…