HCID 67520922, compound → HCID 67521290, compound

HRID 1925907Notes

Reaction equation

HRID 1925907 reaction equation
C([O:3][C:4]([CH:6]1[C:15]([CH2:16][NH:17][C@H:18]([C:23]([O:25][CH3:26])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:14][C:13]2[C:8](=[C:9]([O:29][CH3:30])[CH:10]=[CH:11][C:12]=2[O:27][CH3:28])[O:7]1)=O)C>C(#N)C>[CH3:26][O:25][C:23](=[O:24])[C@@H:18]([N:17]1[CH2:16][C:15]2[CH2:14][C:13]3[C:12]([O:27][CH3:28])=[CH:11][CH:10]=[C:9]([O:29][CH3:30])[C:8]=3[O:7][C:6]=2[C:4]1=[O:3])[CH2:19][CH:20]([CH3:22])[CH3:21]

Participants

3

Reactant 1

HCID 67520922HCID 67520922, compound

Product 1

HCID 67521290HCID 67521290, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5,8-dimethoxy-3-[((S)-1-methoxycarbonyl-3-methyl-butylamino)-methyl]-2H-chromene-2-carboxylic acid ethyl ester (3.0 g, 7.12 mmol) and N,N′-diisopropylethyl amine (5.1 mL, 28.5 mmol) in acetonitrile (4 mL) was heated in a sealed tube at 140° C. for 48 h. The reaction mixture, after aqueous work-up, was extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuo and the residue was purified over neutral alumina using hexanes-ethyl acetate (1:1.2) as eluents to afford (S)-2-(5,8-dimethoxy-3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-4-methyl-pentanoic acid methyl ester (1.4 g, 53.8%) as a solid.

Workup

  1. extractionThe reaction mixture, after aqueous work-up, was extracted with ethyl acetate (3×)
  2. washThe combined ethyl acetate layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe residue was purified over neutral alumina

Sources & evidence

ORD record
ord-ef3262d3e59a4c7c9d4660343d9b1375
Source dataset
uspto-grants-2012_05
Patent number
US08178689B2

Reaction notes

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