Acetyl chloride → HCID 67606271, compound

HRID 1619563Notes

Reaction equation

HRID 1619563 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:31])[CH3:30]>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:31])[CH3:30]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67425463(R)-Quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride

Product 1

HCID 67606271HCID 67606271, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (R)-quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (I25) (140 mg, 0.42 mmol) in DCM (10 ml), were sequentially added triethylamine (175 μl, 1.26 mmol) and acetyl chloride (35.8 μl, 0.50 mmol). The reaction was stirred at RT for 2 hours, and then the solvent was evaporated. The residue was taken up with little EtOAc, and the insoluble was filtered off. The organic phase was evaporated to dryness achieving (R)-quinuclidin-3-yl 2-acetamido-2-phenylacetate (127 mg; quantitative yield).

Workup

  1. customthe solvent was evaporated
  2. filtrationthe insoluble was filtered off
  3. customThe organic phase was evaporated to dryness

Sources & evidence

ORD record
ord-a71cd5be250045358b4e03937065d39b
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

Loading…