Triethylamine → Methyl N-(1,3-benzodioxol-5-ylcarbonyl)-D-tryptophanate

HRID 1837486Notes

Reaction equation

Cl.[CH3:2][O:3][C:4](=[O:17])[C@@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[NH2:6].C(N(CC)CC)C.[C:25](Cl)(=[O:35])[C:26]1[CH:34]=[CH:33][C:32]2[O:31][CH2:30][O:29][C:28]=2[CH:27]=1>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:17])[C@@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[NH:6][C:25]([C:26]1[CH:34]=[CH:33][C:32]2[O:31][CH2:30][O:29][C:28]=2[CH:27]=1)=[O:35]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of D-tryptophan methyl ester hydrochloride (10.2 g) in anhydrous CH2Cl2 (150 ml) cooled at 0° C. was added dropwise triethylamine (12.3 ml). To the resulting solution solid piperonyloyl chloride (8.16 g) was added portionwise at the same temperature, and the mixture was stirred at room temperature for 2 h. The mixture was washed successively with water, 0.5N hydrochloric acid, water, a saturated aqueous solution of NaHCO3 and again with water. After drying over Na2SO4 and evaporation of the solvent under reduced pressure, the resulting oil on trituration from hot cyclohexane afforded the title compound as a white solid (14.7 g).

Workup

washThe mixture was washed successively with water, 0.5N hydrochloric acid, water
dry with materialAfter drying over Na2SO4 and evaporation of the solvent under reduced pressure

Sources & evidence

ORD record: ord-173c5cdea436414694298b3715ac645f
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06784179B2

Reaction notes

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