Methanol → HCID 86730079, compound

HRID 1844402Notes

Reaction equation

HRID 1844402 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].[NH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:15][CH2:14]1.C(N(CC)CC)C.CO>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH2:15][CH2:14]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 723429Tert-butyl (piperidin-4-ylmethyl)carbamate

Product 1

HCID 86730079HCID 86730079, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3,4-dichlorobenzene-1-sulfonyl chloride (470 mg, 1.91 mmol) was added tert-butyl piperidin-4-ylmethylcarbamate (410 mg, 1.91 mmol), followed by triethylamine (0.267 mL, 1.91 mmol). The reaction mixture was stirred overnight then diluted with DCM. The organic phase was washed with 1N HCl, H2O, and brine, dried over Na2SO4, then filtered. The solvent was evaporated under reduced pressure and the residue was purified on a 24 g cartridge using 0 to 100% EtOAc in Hexane and then 0 to 20% MeOH in DCM to yield Intermediate 8A (800 mg, 1.89 mmol, 99% yield). LC-MS (ESI) 324.1. (M+H-Boc), RT=1.55 min (Method B).

Workup

  1. washThe organic phase was washed with 1N HCl, H2O, and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified on a 24 g cartridge

Sources & evidence

ORD record
ord-bd4213742a8344979a8f2288f7cb91fe
Source dataset
uspto-grants-2015_02
Patent number
US08946430B2

Reaction notes

Loading…