Water → HCID 11581759, compound

HRID 1744801Notes

Reaction equation

HRID 1744801 reaction equation
C(O[C:4](=[O:30])/[CH:5]=[CH:6]/[C:7]1[C:8]([NH:16][C:17]2[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:19][CH:18]=2)=[N:9][C:10]([S:14][CH3:15])=[N:11][C:12]=1[CH3:13])C.C1CCN2C(=NCCC2)CC1.O>C(N(CC)C(C)C)(C)C.C1COCC1>[CH3:13][C:12]1[C:7]2[CH:6]=[CH:5][C:4](=[O:30])[N:16]([C:17]3[CH:18]=[CH:19][C:20]([C:21]([O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:22])=[CH:28][CH:29]=3)[C:8]=2[N:9]=[C:10]([S:14][CH3:15])[N:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22225349HCID 22225349, compound

Product 1

HCID 11581759HCID 11581759, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A mixture of compound H (19 g; 0.04423 mol) and DBU (14 mL; 0.0936) in 110 mL of N,N-diisopropylethylamine and 30 mL of THF was refluxed for 30 h. The reaction mixture was poured into 600 mL of iced water and extracted with ethyl acetate (3×500 mL). The organic phase was washed with water and brine, dried over anhydrous sodium sulphate and concentrated. The crude was purified by silica gel column chromatography (eluant: n-hexane/ethyl acetate=2/1 to 1/2) to yield compound 1 (12 g; 71%) as a yellow solid.

Workup

  1. temperaturewas refluxed for 30 h
  2. extractionextracted with ethyl acetate (3×500 mL)
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customThe crude was purified by silica gel column chromatography (eluant: n-hexane/ethyl acetate=2/1 to 1/2)

Sources & evidence

ORD record
ord-e45c06741a074ea2a72181b3f3469b20
Source dataset
uspto-grants-2006_03
Patent number
US07019002B2

Reaction notes

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