D-Tryptophan → HCID 59125421, compound

HRID 1062565Notes

Reaction equation

HRID 1062565 reaction equation
N[C@@H](C(O)=O)CC1C2C(=CC=CC=2)NC=1.O1C2C=CC=CC=2C=C1C=O.[CH3:27][O:28][C:29]([C@@H:31]1[CH2:43][C:42]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[NH:35][C:34]=2[C@H:33]([C:44]2[O:45][C:46]3[CH:52]=[CH:51][CH:50]=[CH:49][C:47]=3[CH:48]=2)[NH:32]1)=[O:30]>>[CH3:27][O:28][C:29]([C@H:31]1[CH2:43][C:42]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[NH:35][C:34]=2[C@H:33]([C:44]2[O:45][C:46]3[CH:52]=[CH:51][CH:50]=[CH:49][C:47]=3[CH:48]=2)[NH:32]1)=[O:30]

Participants

4

Reactant 3

HCID 9060D-TryptophanHCID 613412-BenzofurancarboxaldehydeHCID 59125416HCID 59125416, compound

Product 1

HCID 59125421HCID 59125421, compoundYield 44%

Procedure

Condensation of (R)-(+)-tryptophan with benzo-furan-2-carbaldehyde produced Intermediates 3 and 4 by the same method described above for Intermediates 1 and 2. The crude mixture of diastereomers was separated by chromatography (Biotage 75M, 20% ethyl acetate/80% hexanes) to give 2.85 g (44%) of (1R,3R)-1-benzofuran-2-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester (Intermediate 4) and 950 mg (15%) of (1S,3R)-1-benzofuran-2-yl-2,3,4,9-tetrahydro-1H-p-carboline-3-carboxylic acid methyl ester (Intermediate 3) as foams.

Workup

  1. additionThe crude mixture of diastereomers
  2. customwas separated by chromatography (Biotage 75M, 20% ethyl acetate/80% hexanes)

Sources & evidence

ORD record
ord-290e0b3a24134fad8359722d7e39ffae
Source dataset
uspto-grants-2005_11
Patent number
US06962918B2

Reaction notes

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