Methanol → HCID 86730079, compound

HRID 880021Notes

Reaction equation

HRID 880021 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].N1CC[CH:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:15]C1.C([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])C.CO>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:29]2[CH2:30][CH2:31][CH:15]([CH2:16][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:33][CH2:32]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 8471TriethylamineHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 86730079HCID 86730079, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3,4-dichlorobenzene-1-sulfonyl chloride (490 mg, 2.00 mmol) was added tert-butyl piperidin-4-ylcarbamate (400 mg, 2.00 mmol), followed by triethylamine (0.278 mL, 2.00 mmol). The reaction was stirred at rt overnight. The reaction mixture was diluted with DCM and the organic portion washed with 1N HCl, H2O, and brine, dried over Na2SO4 and decanted. The solvent was evaporated under reduced pressure and the crude residue was purified on a 24 g silica gel cartridge eluting with 0 to 100% EtOAc in hexane, then 0 to 20% MeOH in DCM to provide Intermediate 4A (810 mg, 2.0 mmol, 99% yield). HPLC/MS (Method D) RT=2.12 min, [M+1]+ 309.

Workup

  1. washthe organic portion washed with 1N HCl, H2O, and brine
  2. dry with materialdried over Na2SO4
  3. customdecanted
  4. customThe solvent was evaporated under reduced pressure
  5. customthe crude residue was purified on a 24 g silica gel cartridge
  6. washeluting with 0 to 100% EtOAc in hexane

Sources & evidence

ORD record
ord-d278d425e33540f3a4ad0b213f186cc5
Source dataset
uspto-grants-2015_03
Patent number
US08993557B2

Reaction notes

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