L-Tryptophan → (3S)-1H,2H,3H,4H,9H-pyrido(3,4-b)indole-3-carboxylic acid

HRID 373111Notes

Reaction equation

[NH2:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.N[C@@H:17](C(O)=O)CC1C2C(=CC=CC=2)NC=1>>[CH2:17]1[C:5]2[NH:6][C:7]3[C:12]([C:4]=2[CH2:3][C@@H:2]([C:13]([OH:15])=[O:14])[NH:1]1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

Reactant 2

HCID 6305L-Tryptophan

HCID 9060D-Tryptophan

Product 1

HCID 449440(3S)-1H,2H,3H,4H,9H-pyrido(3,4-b)indole-3-carboxylic acid

Procedure

When L-tryptophan is substituted for D-tryptophan in Example 1E, (3S)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid is obtained.

Sources & evidence

ORD record: ord-544da6888fdf48d6b79a3c763e81716a
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05162336

Reaction notes

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