2-Bromoethanol → HCID 68817820, compound

HRID 736759Notes

Reaction equation

HRID 736759 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:11]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=[C:26]([CH3:34])[CH:25]=3)=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2].Br[CH2:36][CH2:37][OH:38]>C(Cl)Cl>[CH2:1]([O:3][C:4]([CH:6]1[CH:11]([NH:12][S:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=[C:26]([CH3:34])[CH:25]=3)=[CH:20][CH:21]=2)(=[O:15])=[O:14])[CH2:10][CH2:9][N:8]([CH2:36][CH2:37][OH:38])[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 108982-BromoethanolHCID 68819516HCID 68819516, compound

Product 1

HCID 68817820HCID 68817820, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 0.6 g (1.24 mmol) of 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid ethyl ester (see Example 31, Step 1) in CH2Cl2 (10 mL) and TEA (0.313 mL, 3.1 mmol) at 0° C. was added 2-bromoethanol (0.1 mL, 1.36 mmol). The resulting reaction mixture was allowed to warm to 25° C. over 19 h. The reaction was then diluted with CH2Cl2 (50 mL) and washed with 1N HCl (5 mL) and saturated aqueous sodium chloride (30 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by Biotage Flash 40S chromatography, eluting with 2:1 ethyl acetate-hexanes, to provide 1-(2-hydroxy-ethyl)-4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid ethyl ester as a white solid (0.6 g, 92%). MS: 528 (M+H)+

Workup

  1. customThe resulting reaction mixture
  2. washwashed with 1N HCl (5 mL) and saturated aqueous sodium chloride (30 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by Biotage Flash 40S chromatography
  7. washeluting with 2:1 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-0e57911531ff4f458ebeed506921ce5e
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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