Triethylamine → HCID 67607069, compound

HRID 1619520Notes

Reaction equation

HRID 1619520 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:35])[O:30][CH2:31][CH2:32][O:33][CH3:34]>C(Cl)Cl>[CH3:34][O:33][CH2:32][CH2:31][O:30][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:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 694002-Methoxyethyl chloroformateHCID 67425463(R)-Quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride

Product 1

HCID 67607069HCID 67607069, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (R)-quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (I25) (150 mg, 0.45 mmol) in DCM (5 ml), was added triethylamine (188 μl, 1.35 mmol) and 2-methoxyethyl carbonochloridate (63 μl, 0.54 mmol). The reaction was stirred at RT for 4 hours, and then the solvent was evaporated. The residue was taken up with EtOAc, and the organic phase was washed with water and brine, dried over Na2SO4 and evaporated to dryness, obtaining (R)-quinuclidin-3-yl 2-((2-methoxyethoxy)-carbonylamino)-2-phenylacetate (73.0 mg; 45% yield).

Workup

  1. customthe solvent was evaporated
  2. washthe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-d28ef7c0b90b4492bcbd5788b46726db
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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