Triethylamine → HCID 67606166, compound

HRID 1619551Notes

Reaction equation

HRID 1619551 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.[CH3:29][C:30]1[S:31][C:32]([S:36](Cl)(=[O:38])=[O:37])=[C:33]([CH3:35])[N:34]=1>C(Cl)Cl>[CH3:29][C:30]1[S:31][C:32]([S:36]([NH:3][CH:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[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])(=[O:38])=[O:37])=[C:33]([CH3:35])[N:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2776248Dimethyl-1,3-thiazole-5-sulfonyl chlorideHCID 67425463(R)-Quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride

Product 1

HCID 67606166HCID 67606166, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (I25) (116 mg, 0.35 mmol) was suspended in DCM (6 ml), and triethylamine (102 μl, 1.39 mmol) was added obtaining a clear solution. 2,4-Dimethylthiazole-5-sulfonyl chloride (88.0 mg, 0.42 mmol) was added, and the reaction was stirred at RT for 3 hours. The reaction was diluted with DCM and washed with water and brine. The organic phase was dried with Na2SO4, filtered and evaporated to dryness. The crude was purified by flash chromatography (DCM/MeOH=85/15) to obtain (R)-quinuclidin-3-yl 2-(2,4-dimethylthiazole-5-sulfonamido)-2-phenylacetate (67 mg; 44.2% yield).

Workup

  1. customobtaining a clear solution
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude was purified by flash chromatography (DCM/MeOH=85/15)

Sources & evidence

ORD record
ord-2afa39abb80c4f41a9d38702335179c7
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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