HCID 53941766, compound → Ethyl (2S,3S)-2,3-dihydroxy-3-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]propionate

HRID 249363Notes

Reaction equation

HRID 249363 reaction equation
[CH3:1][CH:2]([CH3:32])[CH2:3][C@H:4]([NH:13][C:14]([C@H:16]1[O:20]C(C2C=CC=CC=2)[O:18][C@@H:17]1[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:15])[C:5](=[O:12])[NH:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10]>C(O)(=O)C.[Pd]>[OH:18][C@@H:17]([C@H:16]([OH:20])[C:14](=[O:15])[NH:13][C@H:4]([C:5](=[O:12])[NH:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH2:3][CH:2]([CH3:32])[CH3:1])[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

4

Reactant 1

HCID 53941766HCID 53941766, compound

Product 1

HCID 53688291Ethyl (2S,3S)-2,3-dihydroxy-3-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]propionateYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Ethyl (4S,5S)-5-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]-2-phenyl-1,3-dioxolane-4-carboxylate (2.07 g) obtained in Example 1 was dissolved in acetic acid (40 ml). Palladium black (0.40 g) was added to the resultant solution, and the solution was strongly stirred at room temperature for 60 hours under a hydrogen flow at 4.1 atm. After the catalyst was filtered off, the filtrate was condensed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (a developing solvent; hexane:ethyl acetate=1:1→1:3) to obtain 1.38 g of a target compound. NMR data of the compound was as follows.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. customcondensed under reduced pressure
  3. customto obtain a crude product
  4. customThe crude product was purified by silica gel column chromatography (a developing solvent

Sources & evidence

ORD record
ord-2f062be6ba7e4d25a0fbd8ba329c499f
Source dataset
uspto-grants-1993_05
Patent number
US05214056

Reaction notes

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