HCID 69338406, compound → HCID 20721235, compound

HRID 2086203Notes

Reaction equation

HRID 2086203 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([O:23][C:24](=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C@H:10]([CH3:22])[CH:11]=[CH:12][C:13]1[CH:14]=[CH:15][C:16]2[CH:20]=[CH:19][S:18][C:17]=2[CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][CH:9]([O:23][C:24](=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C@H:10]([CH3:22])[CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]2[CH:20]=[CH:19][S:18][C:17]=2[CH:21]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 69338406HCID 69338406, compound

Product 1

HCID 20721235HCID 20721235, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2R)-t-Butoxycarbonylamino-1-n-hexanoyloxy-2-methyl-4-(benzo[b]thiophen-6-yl)-3-butene (28.0 g, 64.9 mmol) obtained in Example 68(a) was dissolved in methanol (700 ml), and 10% palladium-charcoal (14.0 g) was added thereto followed by stirring for 6 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 under reduced pressure. The residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=15:1-10:1) to give the title compound (24.30 g, 87% 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 under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=15:1-10:1)

Sources & evidence

ORD record
ord-b71820b768564f349592be01dcff8c80
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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