Triethylamine → HCID 86587535, compound

HRID 966519Notes

Reaction equation

HRID 966519 reaction equation
C([O:8]C([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17](C(CO)CCO)[CH:18]=2)[NH:13][C:12]=1C)=O)C1C=CC=CC=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36].CCCCCC.C(OCC)(=[O:47])C>C1COCC1>[S:35]([OH:37])(=[O:47])(=[O:36])[CH3:34].[S:35]([OH:37])(=[O:8])(=[O:36])[CH3:34].[NH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=[CH:12]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21226206Ethyl acetate hexaneHCID 59999370HCID 59999370, compound

Product 1

HCID 86587535HCID 86587535, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(3-Hydroxy-1-hydroxymethyl-propyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.180 g, 0.547 mmol, 1 eq) was suspended in dry THF (5 mL) under Ar. Triethylamine (0.307 mL, 2.2 mmol, 4 eq) was added followed by the addition of methanesulfonyl chloride (0.088 mL, 0.1.09 mmol, 2.0 eq). The reaction mixture was stirred at room temperature. The reaction was followed by TLC (CH2Cl2/MeOH 9/1). After 4 hours, the reaction was quenched with brine and extracted with ethyl acetate (3×). The combined organic extracts were washed with brine and dried over Na2SO4. After removing the solvent, the crude residue was collected. 0.272 g of the indole-bis-mesylate was obtained as a colorless oil. This was carried on crude to the next step.

Workup

  1. customthe reaction was quenched with brine
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customAfter removing the solvent
  6. customthe crude residue was collected

Sources & evidence

ORD record
ord-944469c83a984382928360e4f266820b
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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