Methanol → HCID 86730079, compound

HRID 1053679Notes

Reaction equation

HRID 1053679 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>[C:23]([O:22][C:21](=[O:27])[NH:20][CH2:19][CH:16]1[CH2:15][CH2:14][N:13]([S:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)(=[O:11])=[O:10])[CH2:18][CH2:17]1)([CH3:26])([CH3:24])[CH3:25]

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 99.5%

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 for 16 h then diluted with DCM. The organic phase was washed with 1 N HCl, H2O, and brine, dried over Na2SO4, and 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 hexanes and then 0 to 20% MeOH in DCM to yield Intermediate 9A (0.80 g, 1.9 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 1 N 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-d5d54de44e4a4441a289802063efa1f5
Source dataset
uspto-grants-2016_07
Patent number
US09394260B2

Reaction notes

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