Hydrochloric Acid → HCID 15232184, compound

HRID 1492525Notes

Reaction equation

HRID 1492525 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH:14]([C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[CH2:15][C:16]2[CH:28]=[CH:27][C:19]([CH:20]=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.Cl>CO.C(Cl)Cl.[Ni](Cl)Cl>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH:14]([C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[CH2:15][C:16]2[CH:28]=[CH:27][C:19]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=2)(=[O:11])=[O:12])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 54037641HCID 54037641, compound

Product 1

HCID 15232184HCID 15232184, compound

Reagents, catalysts & solvents 3

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

Nickel chloride (20 mg) was suspended in 1 ml of methanol and 9 ml of methylene chloride, followed by gradual addition of 120 mg of sodium borohydride at 0° C. At the same temperature, ethyl 4-[2-(4-chlorobenzenesulfonamido)-2(3-pyridyl)ethyl]cinnamate dissolved in 0.5 ml of methanol and 4.5 ml of methylene chloride was added and stirred at room temperature for eight hours. To the reaction mixture was added dropwise 2N hydrogen chloride at 0° C., until the mixture became acidic. The organic phase was separated and extracted with methanol-methylene chloride (5:95 v/v). The organic phases were combined and washed in saturated aqueous sodium chloride solution, followed by drying over magnesium sulfate. Then, the solvent was evaporated under reduced pressure. The residue obtained was subjected to chromatography on a silica gel column which was eluted with methanol-methylene chloride (5:95 v/v) for purification, followed by recrystallization in methylene chloride-hexane, to produce 70 mg of ethyl 3-(4-[2-(4-chlorobenzenesulfonamido)-2(3-pyridyl)ethyl]phenyl}propionate. The spectrometric data thereof supports the structure of [24] as follows.

Workup

  1. customThe organic phase was separated
  2. extractionextracted with methanol-methylene chloride (5:95 v/v)
  3. washwashed in saturated aqueous sodium chloride solution
  4. dry with materialby drying over magnesium sulfate
  5. customThen, the solvent was evaporated under reduced pressure
  6. customThe residue obtained
  7. washwas eluted with methanol-methylene chloride (5:95 v/v) for purification
  8. customfollowed by recrystallization in methylene chloride-hexane

Sources & evidence

ORD record
ord-ca1855ee6731485babe13a195d356d0a
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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