Iodoacetic Acid → HCID 19018664, compound

HRID 1110203Notes

Reaction equation

HRID 1110203 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][CH:14]1[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=3[N:16]([CH3:31])[C:15]1=[O:32])=[O:12])=[CH:5]2.I[CH2:34][C:35]([OH:37])=[O:36].[H-].[Na+]>CN(C=O)C>[C:35]([CH2:34][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][CH:14]1[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=3[N:16]([CH3:31])[C:15]1=[O:32])=[O:12])=[CH:5]2)([OH:37])=[O:36]

Participants

5

Reactant 3

HCID 5240Iodoacetic AcidHCID 24758Sodium hydrideHCID 19018663HCID 19018663, compound

Product 1

HCID 19018664HCID 19018664, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,3-Dihydro-3-(5-hydroxyindole-2-carbonylamino)-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one (0.1 g, 0.236 mmol) and iodoacetic acid (0.044 g, 0.236 mmol) were combined in dry DMF (2 ml) and treated with sodium hydride (18.8 mg of a 60% suspension in mineral oil; 0.472 mmol). The mixture was stirred at ambient temperature for 1 hour, then evaporated to dryness in vacuo. To the residue were added water, dilute sodium bisulfite solution, then saturated sodium bicarbonate. The aqueous phase was washed with EtOAc, made acidic with 6N HCl, and extracted with EtOAc. The acid layer extract was dried over sodium sulfate, filtered, and evaporated to dryness in vacuo. The residue was chromatographed on silica gel eluted with 180:10:1:1 of CH2Cl2 :MeOH:HOAc:H2O. The product fractions were evaporated to dryness in vacuo and the residue triturated with ether to give the title compound which was dried in vacuo at 90° C. overnight: (mp 150°-180° C. (↑)).

Workup

  1. customevaporated to dryness in vacuo
  2. additionTo the residue were added water, dilute sodium bisulfite solution
  3. washThe aqueous phase was washed with EtOAc
  4. extractionextracted with EtOAc
  5. extractionThe acid layer extract
  6. dry with materialwas dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo
  9. customThe residue was chromatographed on silica gel
  10. washeluted with 180:10:1:1 of CH2Cl2
  11. customThe product fractions were evaporated to dryness in vacuo
  12. customthe residue triturated with ether

Sources & evidence

ORD record
ord-0ea30117f9804264b5fe187f44988562
Source dataset
uspto-grants-1994_06
Patent number
US05324726

Reaction notes

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