Benzenesulfonyl chloride → 2-(3-Benzenesulfonyloxy-4-methoxy-benzoylamino)-indane-2-carboxylic acid

HRID 521462Notes

Reaction equation

HRID 521462 reaction equation
C[O:2][C:3]([C:5]1([NH:14][C:15](=[O:25])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([OH:24])[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[C:32]1([S:38](Cl)(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(#N)C>[C:32]1([S:38]([O:24][C:18]2[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=2[O:22][CH3:23])[C:15]([NH:14][C:5]2([C:3]([OH:2])=[O:4])[CH2:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:13]2)=[O:25])(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 670765182-(3-Hydroxy-4-methoxy-benzoylamino)-indane-2-carboxylic acid methyl ester

Product 1

HCID 872599092-(3-Benzenesulfonyloxy-4-methoxy-benzoylamino)-indane-2-carboxylic acidYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound of step 2 of example 15 (200 mg, 0.586 mmol) was dissolved in ACN (3 ml), potassium carbonate (243 mg, 1.7 mmol) and benzenesulfonyl chloride (155 mg, 0.88 mmol) were added, and the mixture was stirred for 30 min. The mixture was partitioned between EA and saturated sodium chloride solution, the aqueous phase extracted with EA, and the combined organic extracts were dried over magnesium sulfate, filtered, and evaporated to dryness. The residue was dissolved in dioxane (0.8 ml), lithium hydroxide (0.8 ml of a 1 N aqueous solution) was added, and the mixture was stirred at room temperature for 2.5 h. The mixture was partitioned between 2 N hydrochloric acid and EA, the aqueous phase extracted with EA, and the combined organic extracts were dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified by preparative RP HPLC (water/ACN gradient) to give 115 mg of the title compound.

Workup

  1. customThe mixture was partitioned between EA and saturated sodium chloride solution
  2. extractionthe aqueous phase extracted with EA
  3. dry with materialthe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in dioxane (0.8 ml)
  7. additionlithium hydroxide (0.8 ml of a 1 N aqueous solution) was added
  8. stirringthe mixture was stirred at room temperature for 2.5 h
  9. customThe mixture was partitioned between 2 N hydrochloric acid and EA
  10. extractionthe aqueous phase extracted with EA
  11. dry with materialthe combined organic extracts were dried over magnesium sulfate
  12. filtrationfiltered
  13. customevaporated to dryness
  14. customThe residue was purified by preparative RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-435a054b4e1a4eb6966dcc0d4f22b229
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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