4-Methoxybenzenesulfonyl chloride → HCID 67607656, compound

HRID 1619546Notes

Reaction equation

HRID 1619546 reaction equation
Cl.Cl.[NH2:3][CH:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]([O:7][C@@H:8]1[CH:13]2[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]2)[CH2:9]1)=[O:6].C(N(CC)CC)C.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([Cl:40])(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(Cl)Cl>[ClH:40].[CH3:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([S:37]([NH:3][CH:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]([O:7][C@@H:8]2[CH:13]3[CH2:12][CH2:11][N:10]([CH2:15][CH2:14]3)[CH2:9]2)=[O:6])(=[O:39])=[O:38])=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 67425463(R)-Quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride

Product 1

HCID 67607656HCID 67607656, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (I25) (150 mg, 0.45 mmol) was suspended in DCM (6 ml) and treated with triethylamine (99 μl, 1.35 mmol). Then 4-methoxybenzene-1-sulfonyl chloride (112 mg, 0.54 mmol) was added, and the reaction was stirred at RT for 3 hours. Solvent was evaporated, and the crude was dissolved in EtOAc and washed with water and brine. The organic phase was dried over Na2SO4, filtered and evaporated. The crude was triturated with Et2O to obtain (R)-quinuclidin-3-yl 2-(4-methoxyphenylsulfonamido)-2-phenylacetate hydrochloride (105 mg; 50% yield).

Workup

  1. customSolvent was evaporated
  2. dissolutionthe crude was dissolved in EtOAc
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude was triturated with Et2O

Sources & evidence

ORD record
ord-952e728b79bc43c896c0168419bdfe1b
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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