Acetic Acid → HCID 86586178, compound

HRID 429388Notes

Reaction equation

HRID 429388 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[CH:12]([CH:25]([OH:30])[CH2:26][N+:27]([O-])=O)[CH:13]([NH:21][C:22]([CH3:24])=[O:23])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(O)(=O)C>CO.[Pd]>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[CH:12]([CH:25]([OH:30])[CH2:26][NH2:27])[CH:13]([NH:21][C:22]([CH3:24])=[O:23])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86586176HCID 86586176, compound

Product 1

HCID 86586178HCID 86586178, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(1,2,3,4-tetrahydro-1-oxo-isoquinoline-2-yl)-acetamino-4-hydroxy-5-nitro-pentanoic acid, tert-butyl ester (2.55 g, 6.05 mMol) and 10% Pd on charcoal (1.5 g) in 100 mL of methanol containing 5 mL of 10% aqueous acetic acid was hydrogenated at room temperature for 4 hours. Filtration and evaporation of the solvent under reduced pressure gave of 3-(1,2,3,4-tetrahydro-1-oxo-isoquinoline-2-yl)-acetamino-5-amino-4-hydroxy-pentanoic acid, tert-butyl ester hydroacetate (2.7 g).

Workup

  1. filtrationFiltration and evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-f385885d91c94d90b37884a72407bee7
Source dataset
uspto-grants-2001_11
Patent number
US06316415B1

Reaction notes

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