Hydrochloric Acid → HCID 19962351, compound

HRID 53336Notes

Reaction equation

HRID 53336 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH2:14][CH2:15][C:16]2[CH:17]=[C:18]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])[CH:19]=[C:20]([C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH:21]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.Cl.C(OCC)(=O)C>C(O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][CH2:14][CH2:15][C:16]2[CH:17]=[C:18]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])[CH:19]=[C:20]([CH:22]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[OH:30])[CH:21]=2)(=[O:12])=[O:11])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 199623683-[2-[(4-Chlorophenyl)sulphonylamino]ethyl]-5-(4-fluorobenzoyl)benzenepropanoic acid

Product 1

HCID 19962351HCID 19962351, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.077 g) was added portionwise to a suspension of 3-[2-[(4-chlorophenyl)sulphonylamino]ethyl]-5-(4-fluorobenzoyl)benzenepropanoic acid (0.50 g) in ethanol (12 ml), and the resulting solution was stirred at room temperature for 18 hours. 2N hydrochloric acid (5 ml) was added dropwise followed by ethyl acetate (50 ml), and the mixture was stirred for 1 hour. The organic layer was separated, washed with water and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel. The column was eluted with hexane/ethyl acetate (5:1), followed by hexane/ethyl acetate/acetic acid (50:50:1), gradually increasing the polarity to give a ratio of 10:90:1. The product fractions were combined and evaporated to give the title compound as a gum (0.36 g), Rf 0.45 (SS 15). Found: C,58.58; H,4.71; N,2.65. C24H23ClFNO5S requires C,58.59; H,4.71; N,2.85%.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residue was chromatographed on silica gel
  7. washThe column was eluted with hexane/ethyl acetate (5:1)
  8. temperaturegradually increasing the polarity
  9. customto give a ratio of 10:90:1
  10. customevaporated

Sources & evidence

ORD record
ord-a614f5cea31c4cddabb873dd7a93c038
Source dataset
uspto-grants-1997_04
Patent number
US05618941

Reaction notes

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