Hydrochloric Acid → (R)-1-[4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonyl]-2,3-dihydro-1H-indole-2-carboxylic acid

HRID 351022Notes

Reaction equation

HRID 351022 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]1[C:11]([OH:13])=[O:12].[OH-].[Na+].[CH3:16][C:17]1[O:21][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:19][C:18]=1[CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1.Cl>O1CCOCC1.O>[CH3:16][C:17]1[O:21][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:19][C:18]=1[CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([S:36]([N:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][C@@H:3]2[C:11]([OH:13])=[O:12])(=[O:38])=[O:37])=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 210906794-(5-Methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonyl chlorideHCID 44784971(R)-2,3-dihydro-1H-indole-2-carboxylic acid hydrochloride

Product 1

HCID 10239036(R)-1-[4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonyl]-2,3-dihydro-1H-indole-2-carboxylic acidYield 66.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the title C compound, (R)-2,3-dihydro-1H-indole-2-carboxylic acid hydrochloride (0.92 g, 4.6 mmol), 1N aqueous sodium hydroxide (12.0 mL, 12 mmol) and water (25 mL) at room temperature is added dropwise a solution of 4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonyl chloride (1.65 g, 4.6 mmol) in dioxane (33 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 (11 mL). The precipitate that forms is collected, washed with water and dried under high vacuum overnight to give 1.5 g of (R)-1-[4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonyl]-2,3-dihydro-1H-indole-2-carboxylic acid: [M+1]+=491.2, [M−1]−=489.1

Workup

  1. additionUpon completion of the addition
  2. additionThe solution is poured
  3. custominto crushed ice
  4. customThe precipitate that forms is collected
  5. washwashed with water
  6. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-c1603ba2b0da41038dd0503ced79f73a
Source dataset
uspto-grants-2007_02
Patent number
US07183304B2

Reaction notes

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