HCID 66672612, compound → HCID 66673122, compound

HRID 422918Notes

Reaction equation

HRID 422918 reaction equation
[C:1]([O:4][CH2:5][C@@:6]([NH:27][C:28](=[O:30])[CH3:29])([CH3:26])[CH2:7][CH2:8][C:9]1[N:10]([CH3:25])[C:11]([C:14]#[C:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:13]=1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([O:4][CH2:5][C@@:6]([NH:27][C:28](=[O:30])[CH3:29])([CH3:26])[CH2:7][CH2:8][C:9]1[N:10]([CH3:25])[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 66672612HCID 66672612, compound

Product 1

HCID 66673122HCID 66673122, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2R)-1-acetoxy-2-acetylamino-2-methyl-4-[1-methyl-5-(5-phenylpent-1-ynyl)pyrrol-2-yl]butane (77 mg, 0.19 mmol) obtained in Example (31a) in methanol (2 ml) was added 10% palladium-charcoal (50% wet with water) (4.3 mg), and the resulting mixture was stirred at room temperature under a hydrogen atmosphere for 1 hour. After stirring, the internal atmosphere was replaced with nitrogen, and the palladium-charcoal in the reaction mixture was filtered off using celite, which was washed with ethyl acetate. The filtrate and the washings were combined and evaporated to dryness in vacuo to afford the title compound (75.5 mg, yield: 97%).

Workup

  1. stirringAfter stirring
  2. filtrationthe palladium-charcoal in the reaction mixture was filtered off
  3. washwas washed with ethyl acetate
  4. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-5c2747f87ac84eeeadd59756c80f05f5
Source dataset
uspto-grants-2012_01
Patent number
US08101650B2

Reaction notes

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