Water → 9-Benzenesulfonyl-1,3,4,9-tetrahydro-beta-carboline-2-carboxylic acid benzyl ester

HRID 2063728Notes

Reaction equation

HRID 2063728 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]([N:13]1[CH2:25][CH2:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]=2[CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:26]1([S:32](Cl)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH2:3]([O:10][C:11]([N:13]1[CH2:25][CH2:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([S:32]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:34])=[O:33])[C:15]=2[CH2:14]1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 110667371,3,4,9-Tetrahydro-beta-carboline-2-carboxylic acid benzyl ester

Product 1

HCID 105035369-Benzenesulfonyl-1,3,4,9-tetrahydro-beta-carboline-2-carboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Powdered sodium hydroxide (1.73 g, 43.3 mmol) and tetra-n-butylammonium hydrogen sulfate (111 mg) were added to a solution of the product from stage 1 (6.61 g, 21.6 mmol) in anhydrous methylene chloride (100 ml) and the mixture was stirred at room temperature for 1 h. Benzenesulfonyl chloride (4.21 g, 3.07 ml, 23.8 mmol) was added to the suspension, while cooling with ice. The mixture was stirred at room temperature for 16 h and water and methylene chloride (50 ml of each) were then added. The organic phase was separated off and washed with sodium chloride solution (40 ml). The organic phase was dried with sodium sulfate and concentrated i. vac. The residue was purified by flash chromatography with cyclohexane/ethyl acetate (4:2).

Workup

  1. temperaturewhile cooling with ice
  2. stirringThe mixture was stirred at room temperature for 16 h
  3. customThe organic phase was separated off
  4. washwashed with sodium chloride solution (40 ml)
  5. dry with materialThe organic phase was dried with sodium sulfate
  6. concentrationconcentrated i
  7. customThe residue was purified by flash chromatography with cyclohexane/ethyl acetate (4:2)

Sources & evidence

ORD record
ord-faa9ad6e50e245618692e985a683700e
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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