Methanol → HCID 21201815, compound

HRID 1979452Notes

Reaction equation

HRID 1979452 reaction equation
[C:1]1([C:6]([CH2:8][N:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:12][CH:11]([NH:26][C:27]([NH:29][C:30]3[CH:35]=[CH:34][C:33](C(OCC)=O)=[CH:32][CH:31]=3)=[O:28])[C:10]2=[O:41])=O)[S:5][CH:4]=[CH:3][CH:2]=1.[OH2:42].[OH-:43].[Li+].[CH3:45][OH:46]>O1CCCC1>[C:1]1([C:6]([CH2:8][N:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:12][CH:11]([NH:26][C:27](=[O:28])[NH:29][C:30]3[CH:35]=[C:34]([CH:33]=[CH:32][CH:31]=3)[C:45]([OH:46])=[O:43])[C:10]2=[O:41])=[O:42])[S:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 21201786HCID 21201786, compound

Product 1

HCID 21201815HCID 21201815, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

1-[1-(2-Thenoylmethyl)-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(4-ethoxycarbonylphenyl)urea (0.70 g) was dissolved in tetrahydrofuran (19 ml), aqueous lithium hydroxide monohydrate (0.26 g) solution (15 ml) and methanol (7 ml) were added, the mixture was stirred at 40-50° C. for one hours. The reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid and chloroform were added to the residue, and extracted. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, a mixed solvent of methylene chloride and ether (1:1) was added to powder so precipitated, and collected by filtration,to thereby obtain 0.61 g of the title compound (Yield: 92.4%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid and chloroform
  2. additionwere added to the residue
  3. extractionextracted
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. additiona mixed solvent of methylene chloride and ether (1:1) was added to powder
  8. customso precipitated
  9. filtrationcollected by filtration,to

Sources & evidence

ORD record
ord-5bbbab4aa233464fbc7a9f023ebc9870
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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