4-Chlorobenzenesulfonyl chloride → HCID 67607872, compound

HRID 1619548Notes

Reaction equation

HRID 1619548 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.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>C(Cl)Cl>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([S:36]([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:38])=[O:37])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 67425463(R)-Quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride

Product 1

HCID 67607872HCID 67607872, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (I25) (150 mg, 0.45 mmol) in DCM (5 ml) and triethylamine (190 ul, 1.35 mmol), was added 4-chlorobenzene-1-sulfonyl chloride (114 mg, 0.54 mmol). The reaction was stirred at RT for 3 hours, and then the solvent was evaporated. The crude was taken up with EtOAc and washed with water, brine and then with K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness to obtain (R)-quinuclidin-3-yl 2-(4-chlorophenylsulfonamido)-2-phenylacetate (62 mg; 32% yield), which was used as such in the next step.

Workup

  1. customthe solvent was evaporated
  2. washwashed with water, brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-fafadc1dcb6648a78d274c0b258b6a75
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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