Hydrochloric Acid → HCID 23152774, compound

HRID 1012348Notes

Reaction equation

HRID 1012348 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[NH:20][C:21]2[C:26]([C:27]=1[CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)=[CH:25][CH:24]=[C:23]([C:34]([O:36][CH3:37])=[O:35])[CH:22]=2)[CH2:9][CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:45][S:46](Cl)(=[O:48])=[O:47].Cl>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[NH:20][C:21]2[C:26]([C:27]=1[CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)=[CH:25][CH:24]=[C:23]([C:34]([O:36][CH3:37])=[O:35])[CH:22]=2)[CH2:9][CH2:10][O:11][S:46]([CH3:45])(=[O:48])=[O:47])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23152791methyl 2-(2-{[N-tert-butoxycarbonyl-N-(2-hydroxyethyl)amino]methyl}phenyl)-3-cyclohexyl-1H-indole-6-carboxylate

Product 1

HCID 23152774HCID 23152774, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of methyl 2-(2-{[N-tert-butoxycarbonyl-N-(2-hydroxyethyl)amino]methyl}phenyl)-3-cyclohexyl-1H-indole-6-carboxylate (424 mg, 0.830 mmol) and triethylamine (0.14 ml, 1.0 mmol) in chloroform (5.0 ml) was added dropwise methanesulfonyl chloride (0.07 ml, 0.90 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to give methyl 2-(2-{[N-tert-butoxycarbonyl-N-(2-methanesulfonyloxyethyl)amino]methyl}phenyl)-3-cyclohexyl-1H-indole-6-carboxylate as a crude product. The obtained crude product was used for Step 5 without purification.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-69759eeb55fb440792ea9844266f2085
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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