HCID 69338143, compound → HCID 20721237, compound

HRID 2086201Notes

Reaction equation

HRID 2086201 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([O:19][C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C@H:10]([CH3:18])[CH:11]=[CH:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][CH:9]([O:19][C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C@H:10]([CH3:18])[CH2:11][CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 69338143HCID 69338143, compound

Product 1

HCID 20721237HCID 20721237, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(2R)-t-Butoxycarbonylamino-1-n-hexanoyloxy-2-methyl-4-(thiophen-2-yl)-3-butene (27.6 g, 72.4 mmol) obtained in Example 66(c) was dissolved in ethanol (450 ml), and 10% palladium-charcoal (14.0 g) was added thereto followed by stirring for 4 days at room temperature under a hydrogen atmosphere. After the palladium-charcoal in the reaction solution was filtered out through Celite, the filtrate was evaporated to dryness under reduced pressure. The residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=20:1-10:1) to give the title compound (22.1 g, 80% yield) as a colorless oil.

Workup

  1. filtrationAfter the palladium-charcoal in the reaction solution was filtered out through Celite
  2. customthe filtrate was evaporated to dryness under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=20:1-10:1)

Sources & evidence

ORD record
ord-e8c2f66fb2a54aa08e6b8fb7bd69cda5
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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