Benzenesulfonyl chloride → HCID 67605983, compound

HRID 1619559Notes

Reaction equation

HRID 1619559 reaction equation
Cl.Cl.[NH2:3][CH:4]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[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.[C:30]1([S:36](Cl)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[F:22][C:19]1[CH:18]=[CH:17][C:16]([CH:4]([NH:3][S:36]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(=[O:38])=[O:37])[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])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 67607841HCID 67607841, compound

Product 1

HCID 67605983HCID 67605983, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (R)-quinuclidin-3-yl 2-amino-2-(4-fluorophenyl)acetate dihydrochloride (I82) (325 mg, 0.92 mmol) in DCM (10 ml), were added triethylamine (386 μl, 2.78 mmol) and benzenesulfonyl chloride (142 μl, 1.11 mmol). The reaction was stirred at RT for 4 hours, and then the solvent was evaporated. The residue was taken up with EtOAc and washed with 1M Na2CO3, water and then brine, dried over Na2SO4 and evaporated to dryness to obtain (R)-quinuclidin-3-yl 2-(4-fluorophenyl)-2-(phenylsulfonamido)acetate (150 mg; 39% yield).

Workup

  1. customthe solvent was evaporated
  2. washwashed with 1M Na2CO3, water
  3. dry with materialbrine, dried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-60d9824daae243a581a2a301d70adf7f
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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