3-Hydroxybenzaldehyde → HCID 67442708, compound

HRID 1666286Notes

Reaction equation

HRID 1666286 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]([NH2:16])([CH3:15])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1.[OH:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O.FC(F)(F)C(O)=O>>[CH3:1][O:2][C:3]([C:4]1([CH3:15])[CH2:5][C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[CH:22]([C:21]2[CH:24]=[CH:25][CH:26]=[C:19]([OH:18])[CH:20]=2)[NH:16]1)=[O:17]

Participants

4

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 6422Trifluoroacetic acidHCID 2795140Methyl alpha-methyltryptophanate

Product 1

HCID 67442708HCID 67442708, compoundYield 14%

Procedure

1.00 g (4.30 mmol) of the commercially available 2-amino-3-(1H-indol-3-yl)-2-methyl-propionic acid methyl ester are reacted with 600 mg (4.73 mmol) 3-hydroxy-benzaldehyde in the presence of trifluoroacetic acid according to the Pictet-Spengler reaction. The resulting mixture of diastereomers is separated by column chromatography (toluene, ethyl acetate 4:1). 1.17 g (68%) of the title compound and 320 mg (14%) of (1SR,3SR)-1-(3-hydroxy-phenyl)-3-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester (compound A2) are obtained as white solids.

Workup

  1. additionThe resulting mixture of diastereomers
  2. customis separated by column chromatography (toluene, ethyl acetate 4:1)

Sources & evidence

ORD record
ord-b4ce2a9058ff46709a85a7094e301460
Source dataset
uspto-grants-2011_10
Patent number
US08044065B2

Reaction notes

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