Triethylamine → Cbz-aminoglutarimide

HRID 533359

Reaction equation

HRID 533359 reaction equation
N1[CH:6]=[CH:5][C:4]2[C:7]([O:9][C:10](=[O:11])[C:3]=2[CH:2]=1)=O.[NH2:12][CH:13]1[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:14]1=[O:15].[CH2:21](N(CC)CC)C>>[C:10]([C:13]1([NH2:12])[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:14]1=[O:15])([O:9][CH2:7][C:4]1[CH:5]=[CH:6][CH:21]=[CH:2][CH:3]=1)=[O:11]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 1345083-Amino-2,6-piperidinedioneHCID 2783981H,3H-furo(3,4-c)pyridine-1,3-dione

Product 1

HCID 67017964Cbz-aminoglutarimideYield 17%

Procedure

With reference to Scheme 4 below, azathalidomide was prepared from aminoglutarimide and commercial pyridine-3,4-dicarboxylic anhydride. Cbz-aminoglutarimide was deprotected by hydrogenolysis with catalyst palladium hydroxide on carbon (10%) to form aminoglutarimide. Pyridine-3,4-dicarboxyic anhydride was refluxed with aminoglutarimide in the presence of triethylamine to yield azathalidomide 11 in the total yield of 17% from Cbz-aminoglutarimide.

Sources & evidence

ORD record
ord-ce699545f7fa4c82baa51d40f8c107be
Source dataset
uspto-grants-2014_10
Patent number
US08853253B2

Linked notes

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