2-Carboxyoctahydroindole, (2S,3aS,7aS)- → L-Alanine

HRID 2072816Notes

Reaction equation

HRID 2072816 reaction equation
[C:1]([C@@H:4]1[CH2:12][C@H:11]2[C@H:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[NH:5]1)([OH:3])=[O:2].[C:13]([C@@H:18]([NH:22][C@H](C(O)=O)C)[CH2:19]CC)([O:15]CC)=[O:14]>>[C:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)([OH:3])=[O:2].[NH2:22][C@H:18]([C:13]([OH:15])=[O:14])[CH3:19]

Participants

4

Reactant 2

HCID 74084522-Carboxyoctahydroindole, (2S,3aS,7aS)-HCID 10015159(2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acid

Product 2

HCID 5950L-AlanineHCID 72899Indole-2-carboxylic acid

Procedure

The (2S,3aS,7aS)-2-carboxyperhydroindole and N-[(S)-1-carbethoxybutyl]-(S)-alanine are themselves obtained in excellent conditions from 2-carboxyindole and from L-alanine respectively, both available on an industrial scale.

Sources & evidence

ORD record
ord-b76b9f3395c946edb8192f7a5f05a63b
Source dataset
uspto-grants-1990_04
Patent number
US04914214

Reaction notes

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