Succinic Acid → HCID 71608767, compound

HRID 1847126Notes

Reaction equation

HRID 1847126 reaction equation
C([NH:11][CH2:12][CH2:13][S:14]([NH2:17])(=[O:16])=[O:15])(OCC1C=CC=CC=1)=O.[C:18]([OH:25])(=[O:24])[CH2:19][CH2:20][C:21]([OH:23])=[O:22]>CO.[Pd]>[C:18]([OH:25])(=[O:24])[CH2:19][CH2:20][C:21]([OH:23])=[O:22].[NH2:11][CH2:12][CH2:13][S:14]([NH2:17])(=[O:16])=[O:15]

Participants

5

Reactant 2

HCID 1110Succinic AcidHCID 11615848Phenylmethyl N-[2-(aminosulfonyl)ethyl]carbamate

Product 1

HCID 71608767HCID 71608767, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Take a suspension of 100 g of Cbz-Taurinamide in 1000 ml methanol, and 10% Pd/C (1.0 g) and subject to hydrogenation at 45-50 psi. Upon completion of the reaction filter the catalyst and add succinic acid (1.0 eq) to the solvent and distill off the solvent under vacuum to provide the title compound in about 90% yield as a white solid.

Workup

  1. filtrationUpon completion of the reaction filter the catalyst
  2. distillationdistill off the solvent under vacuum

Sources & evidence

ORD record
ord-813d380eab574ec4bedaa30dcf3265a5
Source dataset
uspto-grants-2015_02
Patent number
US08952148B2

Reaction notes

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