Acetic Anhydride → HCID 59446546, compound

HRID 1510323Notes

Reaction equation

HRID 1510323 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH2:22][P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH2:17][CH2:16]3)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32].[OH-].[Na+]>ClCCl>[C:31]([N:18]1[C:19]2[C:15](=[CH:14][C:13]([N:12]([CH2:22][P:23](=[O:30])([O:24][CH2:25][CH3:26])[O:27][CH2:28][CH3:29])[S:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)(=[O:10])=[O:11])=[CH:21][CH:20]=2)[CH2:16][CH2:17]1)(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 59446513HCID 59446513, compound

Product 1

HCID 59446546HCID 59446546, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.45 g diethyl {[(3,5-dichloro-phenylsulphonyl)-(2,3-dihydro-1H-indol-5-yl)-amino]-methyl}-phosphonate are dissolved in 20 ml dichloromethane, combined with 2 ml acetic anhydride and stirred for 2 hours at ambient temperature. The mixture is diluted with dichloromethane, cooled to 0° C. and 20 ml of 4 N sodium hydroxide solution are added thereto. After stirring for 30 minutes the phases are separated and the organic phase is washed with saturated sodium chloride solution. Then it is dried on magnesium sulphate, the solvents are eliminated in vacuo and the residue is chromatographed on silica gel (dichloromethane/methanol 95:5 to 75:25).

Workup

  1. temperaturecooled to 0° C.
  2. stirringAfter stirring for 30 minutes the phases
  3. customare separated
  4. washthe organic phase is washed with saturated sodium chloride solution
  5. customThen it is dried on magnesium sulphate
  6. customthe residue is chromatographed on silica gel (dichloromethane/methanol 95:5 to 75:25)

Sources & evidence

ORD record
ord-ab4efc6b3ffe43bc8bec7627c40cb160
Source dataset
uspto-grants-2012_07
Patent number
US08211923B2

Reaction notes

Loading…