HCID 86744053, compound → HCID 18639816, compound

HRID 1031250Notes

Reaction equation

HRID 1031250 reaction equation
[C:1]([S:4][CH:5]([CH:17]([C:22]([NH:24][C@H:25]([C:35]([NH:37][CH3:38])=[O:36])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:6][C:7]([O:9]CC1C=CC=CC=1)=[O:8])(=[O:3])[CH3:2]>C(O)=O.CO.[Pd]>[C:1]([S:4][CH:5]([CH:17]([C:22]([NH:24][C@H:25]([C:35]([NH:37][CH3:38])=[O:36])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:6][C:7]([OH:9])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86744053HCID 86744053, compound

Product 1

HCID 18639816HCID 18639816, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18963719Formic acid methanolSolvent

Procedure

A solution of 3-acetylmercapto-6-methyl-4-[[[1-(S)-[(methylamino)carbonyl]-2-(4-methoxyphenyl)ethyl]amino]carbonyl]heptanoic acid, benzyl ester (E3; 300 mg, 0.55 mmol) in 4.5% formic acid/methanol (6 ml) was added, under nitrogen, to a stirred suspension of palladium black (310 mg) in the same solvent (15 ml). After 90 min the mixture was filtered through kieselguhr and evaporated in vacuo. Column chromatography using reverse phase silica (30 g) and eluting with 25% aqueous methanol gave two single diastereoisomers of the title compound, as monohydrates.

Workup

  1. filtrationAfter 90 min the mixture was filtered through kieselguhr
  2. customevaporated in vacuo
  3. washeluting with 25% aqueous methanol

Sources & evidence

ORD record
ord-abc918b1246f42779e92648375106cea
Source dataset
uspto-grants-1992_04
Patent number
US05109000

Reaction notes

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