Triethylamine → HCID 67606490, compound

HRID 1619554Notes

Reaction equation

HRID 1619554 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.[F:29][C:30]([F:37])([F:36])[CH2:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[C:16]1([CH:4]([NH:3][S:32]([CH2:31][C:30]([F:37])([F:36])[F:29])(=[O:34])=[O:33])[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][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 67425463(R)-Quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride

Product 1

HCID 67606490HCID 67606490, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (R)-quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (I25) (120 mg, 0.36 mmol) in DCM (4 ml) and triethylamine (105 μl, 1.44 mmol), was added 2,2,2-trifluoroethanesulfonyl chloride (47.5 μl, 0.43 mmol). The reaction was stirred at RT for 3 hours, and then it was diluted with DCM and washed with water, brine and 1M K2CO3. The organic phase was dried with Na2SO4, filtered, and evaporated. The crude was purified with flash chromatography (DCM/MeOH=9/1) to obtain (R)-quinuclidin-3-yl 2-phenyl-2-(2,2,2-trifluoroethylsulfonamido)acetate (60 mg; 41% yield).

Workup

  1. washwashed with water, brine and 1M K2CO3
  2. dry with materialThe organic phase was dried with Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude was purified with flash chromatography (DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-e8316a4840474921aefc6c5253294e07
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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