Triethylamine → HCID 11292109, compound

HRID 2403258Notes

Reaction equation

HRID 2403258 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[C:13]([O:17][C:18](=[O:34])[N:19]([CH2:23][C:24]1[CH:25]=[C:26]([F:33])[CH:27]=[C:28]2[C:32]=1[NH:31][CH:30]=[CH:29]2)[CH2:20][CH2:21][OH:22])([CH3:16])([CH3:15])[CH3:14]>ClCCl.C(OCC)(=O)C>[C:13]([O:17][C:18]([N:19]([CH2:23][C:24]1[CH:25]=[C:26]([F:33])[CH:27]=[C:28]2[C:32]=1[NH:31][CH:30]=[CH:29]2)[CH2:20][CH2:21][O:22][S:9]([CH3:8])(=[O:11])=[O:10])=[O:34])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11243760HCID 11243760, compound

Product 1

HCID 11292109HCID 11292109, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Add triethylamine (4.64 mL, 33.3 mmol) followed by methanesulfonyl chloride (1.29 mL, 16.65 mmol) to a solution of (5-fluoro-1H-indol-7-ylmethyl)-(2-hydroxyethyl)-carbamic acid tert-butyl ester (4.9 g, assume 15.14 mmol) in dichloromethane (70 mL) at 0° C. Stir the reaction mixture for 30 minutes at 0° C. Dilute with ethyl acetate (200 mL), wash with sequentially with saturated aqueous sodium bicarbonate (200 mL×3) and saturated aqueous sodium chloride (200 mL×2). Dry the organic phase over sodium sulfate and concentrate under reduced pressure to provide the desired compound as a yellow brown oil (5.9 g, >100%).

Workup

  1. washwash with sequentially with saturated aqueous sodium bicarbonate (200 mL×3) and saturated aqueous sodium chloride (200 mL×2)
  2. dry with materialDry the organic phase over sodium sulfate
  3. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-f7ca68b9647f44cd8baa8ce922adf4f1
Source dataset
uspto-grants-2014_08
Patent number
US08802668B2

Reaction notes

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