Acetic Acid → HCID 53905499, compound

HRID 1651878Notes

Reaction equation

HRID 1651878 reaction equation
C([O-])(C)(C)C.[K+].Cl[CH2:8][C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH:15]([NH:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22])[CH2:14]2)=[O:10].[C:31]([O:39][CH2:40][CH3:41])(=[O:38])[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].C(O)(=O)C>CS(C)=O.O>[C:31]([CH:32]([CH2:8][C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH:15]([NH:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22])[CH2:14]2)=[O:10])[C:33]([O:35][CH2:36][CH3:37])=[O:34])([O:39][CH2:40][CH3:41])=[O:38]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 23665647Potassium tert-butoxideHCID 54104191HCID 54104191, compound

Product 1

HCID 53905499HCID 53905499, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

10.6 g (0.095 mol) of potassium tert.-butanolate, followed by 23.0 g (0.063 mol) of (2-p-toluenesulphonamido-indan-5-yl) chloromethyl ketone, are added to 15.2 g (0.095 mol) of diethyl malonate in 25 ml of dimethyl sulphoxide. The mixture is allowed to stand overnight and is neutralised with glacial acetic acid, and water and petroleum ether are added. The reaction product which is precipitated is separated off and dissolved in ethyl acetate. The organic phase is washed with water, dried and evaporated, and the residue obtained is purified by chromatography over 600 g of silica gel using 98:2 ethylene chloride/ethanol.

Workup

  1. additionare added
  2. customThe reaction product which is precipitated
  3. customis separated off
  4. dissolutiondissolved in ethyl acetate
  5. washThe organic phase is washed with water
  6. customdried
  7. customevaporated
  8. customthe residue obtained
  9. customis purified by chromatography over 600 g of silica gel using 98:2 ethylene chloride/ethanol

Sources & evidence

ORD record
ord-edc07604cbe248ef9cc188c32053b924
Source dataset
uspto-grants-1990_05
Patent number
US04929754

Reaction notes

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