Benzoyl chloride → (R)-quinuclidin-3-yl 2-benzamido-2-phenylacetate

HRID 1619562Notes

Reaction equation

HRID 1619562 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.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[C:29]([NH: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[CH2:12][CH2:11][N:10]([CH2:15][CH2:14]2)[CH2:9]1)=[O:6])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 67425463(R)-Quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride

Product 1

HCID 67605943(R)-quinuclidin-3-yl 2-benzamido-2-phenylacetateYield 42.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (R)-quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (I25) (0.67 g, 2.01 mmol) in DCM (25 ml), were sequentially added triethylamine (0.84 ml, 6.04 mmol) and benzoyl chloride (0.28 ml, 2.42 mmol). The reaction was stirred at RT for 4 hours, and then the solvent was evaporated. The crude was taken up with EtOAc and washed with water and brine, dried over Na2SO4 and evaporated to obtain (R)-quinuclidin-3-yl 2-benzamido-2-phenylacetate (310 mg; 42% yield).

Workup

  1. customthe solvent was evaporated
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-78d4751773994a8f8d28b838ad8280ac
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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