HCID 19352281, compound → HCID 10868373, compound

HRID 1636637Notes

Reaction equation

HRID 1636637 reaction equation
C(OC([NH:11][C:12]1[C:13](=[O:27])[O:14][CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:18]=2[O:25][CH3:26])[CH:16]=1)=O)C1C=CC=CC=1>[Pd]>[NH2:11][CH:12]([CH2:16][CH2:15][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:18]=1[O:25][CH3:26])[C:13]([OH:27])=[O:14]

Participants

3

Reactant 1

HCID 19352281HCID 19352281, compound

Product 1

HCID 10868373HCID 10868373, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The step consists in the catalytic hydrogenation of 3-benzyloxycarbonylamino-5-(2,3-dimethoxyphenyl)-2,5-dihydrofuran-2-one, for example with palladium on carbon as catalyst in alcoholic medium, thus obtaining directly in a single step the deprotected 2-amino-4-(2,3-dimethoxyphenyl)butyric acid. The reaction takes place in nearly quantitative yields. The reaction, as already discussed in the above process, can be carried out under enantioselectivity conditions, to obtain 2-amino-4-(2,3-dimethoxyphenyl)butyric acid in an optically active form.

Sources & evidence

ORD record
ord-bf4172861429425fb8a870b76e2a7a43
Source dataset
uspto-grants-2000_03
Patent number
US06034277

Reaction notes

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