Hydrochloric Acid → HCID 67436128, compound

HRID 351016Notes

Reaction equation

HRID 351016 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]1[C:10]([OH:12])=[O:11].[OH-].[Na+].[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>O.O1CCOCC1>[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][C@@H:2]2[C:10]([OH:12])=[O:11])(=[O:31])=[O:30])=[CH:25][CH:24]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 47383854-(Benzyloxy)benzene-1-sulfonyl chlorideHCID 6928266(R)-Indoline-2-carboxylic acid

Product 1

HCID 67436128HCID 67436128, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-2,3-dihydro-1H-indole-2-carboxylic acid (2.89 g, 14.5 mmol) and 1N sodium hydroxide (37.7 mL, 37.7 mmol) in water (79 mL) stirring at room temperature is added dropwise a solution of 4-benzyloxybenzenesulfonyl chloride (4.1 g, 14.5 mmol) in dioxane (104 mL). Upon completion of the addition, the pH of the reaction mixture is monitored and maintained between 7–8 by slow addition of 1N aqueous sodium hydroxide over the next 2 hours. The reaction mixture is stirred overnight at room temperature. The solution is poured into crushed ice and the resulting mixture is acidified to pH 2–3 with 1N aqueous hydrochloric acid (15 mL). The product is extracted into dichloromethane (2×150 mL). The extract is washed with water (150 mL), brine (150 mL), dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated to give 5.5 g of (R)-1-(4-benzyloxy-benzenesulfonyl)-2,3-dihydro-1H-indole-2-carboxylic acid as an oil: [M+1]+=410.32, [M−1]−=408.24.

Workup

  1. additionUpon completion of the addition
  2. additionThe solution is poured
  3. custominto crushed ice
  4. extractionThe product is extracted into dichloromethane (2×150 mL)
  5. washThe extract is washed with water (150 mL), brine (150 mL)
  6. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cc35c2f15e5f4eae9612f957e5cffbe5
Source dataset
uspto-grants-2007_02
Patent number
US07183304B2

Reaction notes

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