Benzoyl chloride → HCID 67606235, compound

HRID 1619568Notes

Reaction equation

HRID 1619568 reaction equation
Cl.Cl.[NH2:3][CH:4]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[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](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl>[C:30]([NH:3][CH:4]([C:16]1[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=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:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 67607082HCID 67607082, compound

Product 1

HCID 67606235HCID 67606235, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (R)-quinuclidin-3-yl 2-amino-2-p-tolylacetate dihydrochloride (I109) (116 mg, 0.33 mmol) in DCM (5 ml), were added triethylamine (139 μl, 1.00 mmol) and benzoyl chloride (46.5 μl, 0.40 mmol). The reaction was stirred at RT for 3 hours, and then the solvent was evaporated. The residue was taken up with EtOAc and washed with Na2CO3, water and brine. The organic phase was dried over Na2SO4, filtered and evaporated to obtain (R)-quinuclidin-3-yl 2-benzamido-2-p-tolylacetate (70.0 mg; 55% yield). The product was used in the next step without any further purification.

Workup

  1. customthe solvent was evaporated
  2. washwashed with Na2CO3, water and brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-90564dfa511a409a85582daeca368ce1
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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