HCID 15078404, compound → HCID 15078407, compound

HRID 1110439Notes

Reaction equation

HRID 1110439 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:21][CH2:22][C:23]([NH:25][CH2:26][CH2:27][C:28]([O:30]C)=[O:29])=[O:24])[CH:18]=3)[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>CO.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:21][CH2:22][C:23]([NH:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:24])[CH:18]=3)[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 15078404HCID 15078404, compound

Product 1

HCID 15078407HCID 15078407, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

818 mg of methyl 3-{[2-[(4-chlorophenyl)sulfonylamino]indan-5-yl]oxyacetylamino}propionate are dissolved in 10 ml of methanol, and an aqueous In sodium hydroxide solution is added to the solution. The mixture is stirred at room temperature for 3 hours. The reaction mixture is evaporated to remove methanol and the residue is acidified with an aqueous 10% hydrochloric acid solution. The mixture is extracted with ethyl acetate. The extract is washed successively with an aqueous saturated sodium hydrochloride solution, dried and evaporated to remove solvent. The residue is recrystallized from a mixture of tetrahydrofuran and isopropyl ether to give 750 mg of 3-{[2-[(4-chlorophenyl)sulfonylamino]indan-5-yl]oxyacetylamino}propionic acid as colorless prisms. Yield: 92%

Workup

  1. customThe reaction mixture is evaporated
  2. customto remove methanol
  3. extractionThe mixture is extracted with ethyl acetate
  4. washThe extract is washed successively with an aqueous saturated sodium hydrochloride solution
  5. customdried
  6. customevaporated
  7. customto remove solvent
  8. customThe residue is recrystallized from a mixture of tetrahydrofuran and isopropyl ether

Sources & evidence

ORD record
ord-debe6522e9db4af8b623e9da7265a3e2
Source dataset
uspto-grants-1990_12
Patent number
US04975460

Reaction notes

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