HCID 14032380, compound → HCID 13773274, compound

HRID 1651449Notes

Reaction equation

HRID 1651449 reaction equation
[C:1]([C:5]1[S:9][C@@H:8]([C:10]([O:12]CC2C=CC=CC=2)=[O:11])[N:7]([C:20](=[O:33])[C@H:21]([CH3:32])[NH:22][C@H:23]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:24][CH2:25][CH3:26])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([C:5]1[S:9][C@@H:8]([C:10]([OH:12])=[O:11])[N:7]([C:20](=[O:33])[C@H:21]([CH3:32])[NH:22][C@H:23]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:24][CH2:25][CH3:26])[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 14032380HCID 14032380, compound

Product 1

HCID 13773274HCID 13773274, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The S,S,S benzyl ester from step (e) (1.8g) in ethanol (500ml) was hydrogenated over 10% Pd on charcoal (1.8g) at atmospheric pressure and room temperature for 5 hours. The catalyst was removed by filtration and the filtrate was evaporated to dryness. The residue was triturated with a 1:1 mixture of ether/petroleum ether 60°-80° to give the required acid as a white solid (1.3g). mp 183°-5°.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was triturated with a 1:1 mixture of ether/petroleum ether 60°-80°

Sources & evidence

ORD record
ord-0fe6295c4f4945da833f1360892511e9
Source dataset
uspto-grants-1990_05
Patent number
US04927822

Reaction notes

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