Sodium Hydroxide → HCID 18612994, compound

HRID 1264601Notes

Reaction equation

HRID 1264601 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]([CH2:23][CH2:24][O:25][CH3:26])[CH2:14][CH:13]2[C:27]([O:29]C)=[O:28])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]([CH2:23][CH2:24][O:25][CH3:26])[CH2:14][CH:13]2[C:27]([OH:29])=[O:28])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18612750HCID 18612750, compound

Product 1

HCID 18612994HCID 18612994, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.0 g (2.3 mmol) of methyl 4-(4-methoxybenzenesulfonyl)-1-(2-methoxyethyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate and 3.0 ml of 1 N NaOH in 10 ml of tetrahydrofuran was stirred at room temperature for 2 hours and the solvent removed. To the residue was added water and the mixture acidified with 1 N HCl. The mixture was extracted with ethyl acetate and the extract was washed with brine and dried with Na2SO4. The solvent was removed and the residue triturated with ethyl acetate-hexane, cooled and filtered to give 0.65 g of white crystals, m.p. 164°-165° C.; Mass spectrum (ES) 421.4 (M+H). Anal. for C20H24N2O6S: Calc'd: C, 57.1; H, 5.8; N, 6.7; Found: C, 57.3; H, 5.7; N, 6.4.

Workup

  1. customthe solvent removed
  2. additionTo the residue was added water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with brine
  5. dry with materialdried with Na2SO4
  6. customThe solvent was removed
  7. customthe residue triturated with ethyl acetate-hexane
  8. temperaturecooled
  9. filtrationfiltered

Sources & evidence

ORD record
ord-60e1fb6fc8b74d7583c2f348ed81287b
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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