Acetic Acid → HCID 54061321, compound

HRID 223335Notes

Reaction equation

HRID 223335 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH2:16][C@H:15](CS([O-])(=O)=O)[CH2:14][C@H:10]3[C:11](=[O:13])[NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C(O)(=O)C>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH:16]=[CH:15][CH2:14][C@H:10]3[C:11](=[O:13])[NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 86738591HCID 86738591, compound

Product 1

HCID 54061321HCID 54061321, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 17.0 g (49.3 mmol) of (2R,11aS)-6-chloro-2,3,5,10,11,11a-hexahydro-5,11-dioxo-1H-pyrrolo[2,1-c][1,4]benzodiazepin-2-yl-methanesulphonate in 80 ml of dry dimethylformamide is treated with 4.3 g (98.6 mmol) of sodium hydride (55 percent oil dispersion), the mixture is stirred at 45° for a further 2 hours, then poured into 300 ml of ice-water, neutralized with 5.6 ml of glacial acetic acid and extracted four times with methylene chloride. The organic extracts are washed once with saturated sodium chloride solution, dried over magnesium sulphate and evaporated. By crystallization from ethanol there is obtained (S)-6-chloro-1,11a-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione of melting point 249°-251°.

Workup

  1. extractionextracted four times with methylene chloride
  2. washThe organic extracts are washed once with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customBy crystallization from ethanol

Sources & evidence

ORD record
ord-b7df2185bfd04b408e2b14d4a9353cb7
Source dataset
uspto-grants-1982_10
Patent number
US04353827

Reaction notes

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