HCID 178501250, compound → HCID 178501249, compound

HRID 1944705Notes

Reaction equation

HRID 1944705 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:22]([O-])=O>C(O)(=O)C.[Zn]>[NH2:22][C:3]1[CH:4]=[C:5]([S:8]([NH:11][C@H:12]2[CH2:13][CH2:14][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH2:17]2)(=[O:9])=[O:10])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 1

HCID 178501250HCID 178501250, compound2×

Product 1

HCID 178501249HCID 178501249, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Zinc dust (1345 mg, 20.57 mmol) was added to a room temperature solution of methyl trans-4-(4-chloro-3-nitrophenylsulfonamido)cyclohexanecarboxylate (Intermediate 1, 775 mg, 2.057 mmol) in acetic acid (15.200 ml). The reaction was heated to 50° C. overnight, the filtered over celite and rinsed with acetic acid. The acetic acid was removed in vacuo at 60° C., and the residue was partitioned between EtOAc/sat'd NaHCO3. The aqueous layer was extracted with a second portion EtOAc, and the organic layers were combined then rinsed 1× brine, dry over MgSO4, filter, and concentrated to give the title compound as a solid (670 mg, 1.932 mmol, 94% yield). MS MH+ 347.1

Workup

  1. filtrationthe filtered over celite
  2. washrinsed with acetic acid
  3. customThe acetic acid was removed in vacuo at 60° C.
  4. customthe residue was partitioned between EtOAc/
  5. extractionThe aqueous layer was extracted with a second portion EtOAc
  6. washthe organic layers were combined then rinsed 1× brine
  7. dry with materialdry over MgSO4
  8. filtrationfilter
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d5680f82306e477e9d93563b81296589
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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