Sodium Phosphate, Dibasic → 2-[4-Cyclopropoxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid

HRID 521526Notes

Reaction equation

HRID 521526 reaction equation
ClC1C=CC=C(C(OO)=O)C=1.C1(S[C:19]2([O:22][C:23]3[CH:43]=[CH:42][C:26]([C:27]([NH:29][C:30]4([C:39]([OH:41])=[O:40])[CH2:38][C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[CH2:31]4)=[O:28])=[CH:25][C:24]=3[O:44][CH2:45][CH2:46][C:47]3[CH:48]=[C:49]([CH3:53])[CH:50]=[CH:51][CH:52]=3)[CH2:21][CH2:20]2)C=CC=CC=1.P([O-])([O-])(O)=O.[Na+].[Na+]>C(Cl)Cl.C(=O)([O-])O.[Na+].[Na].[Hg]>[CH:19]1([O:22][C:23]2[CH:43]=[CH:42][C:26]([C:27]([NH:29][C:30]3([C:39]([OH:41])=[O:40])[CH2:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:31]3)=[O:28])=[CH:25][C:24]=2[O:44][CH2:45][CH2:46][C:47]2[CH:48]=[C:49]([CH3:53])[CH:50]=[CH:51][CH:52]=2)[CH2:20][CH2:21]1

Participants

7

Reactant 3

HCID 24203Sodium Phosphate, DibasicHCID 70297m-Chloroperbenzoic acidHCID 670763202-[4-(1-Phenylsulfanyl-cyclopropoxy)-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid

Product 1

HCID 670766922-[4-Cyclopropoxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid

Reagents, catalysts & solvents 3

HCID 9837419Sodium amalgamCatalystHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-Chloroperbenzoic acid (43 mg, 0.177 mmol) was added to the compound of step 1 (35 mg, 0.059 mmol) in DCM (2 ml) and saturated aqueous sodium hydrogencarbonate solution (2 ml). The mixture was stirred for 30 min at room temperature and then partitioned between EA and a sodium carbonate solution. The aqueous phase was extracted with EA and the combined organic phases were dried over sodium sulfate and evaporated to dryness. The residue (44 mg) was dissolved in a mixture of 0.5 ml of THF and 1 ml of methanol. Disodium hydrogenphosphate (40 mg, 0.28 mmol) and sodium mercury amalgam (5% sodium) (250 mg) were added and the mixture was stirred for 30 min at room temperature and stored for 6 days at 5° C. Then 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 sodium chloride, decanted and evaporated to dryness. The residue was purified by silica gel chromatography (DCM/methanol/28% ammonia gradient, 90:10:1 to 85:15:1.5). The product fractions were evaporated to dryness and the residue partitioned between 2 N hydrochloric acid and EA. The aqueous phase was extracted with EA, and the combined organic extracts were dried over sodium chloride, decanted and evaporated to dryness.

Workup

  1. custompartitioned between EA
  2. extractionThe aqueous phase was extracted with EA
  3. dry with materialthe combined organic phases were dried over sodium sulfate
  4. customevaporated to dryness
  5. dissolutionThe residue (44 mg) was dissolved in a mixture of 0.5 ml of THF and 1 ml of methanol
  6. stirringthe mixture was stirred for 30 min at room temperature
  7. waitstored for 6 days at 5° C
  8. customThen the mixture was partitioned between 2 N hydrochloric acid and EA
  9. extractionthe aqueous phase extracted with EA
  10. dry with materialthe combined organic extracts were dried over sodium chloride
  11. customdecanted
  12. customevaporated to dryness
  13. customThe residue was purified by silica gel chromatography (DCM/methanol/28% ammonia gradient, 90:10:1 to 85:15:1.5)
  14. customThe product fractions were evaporated to dryness
  15. customthe residue partitioned between 2 N hydrochloric acid and EA
  16. extractionThe aqueous phase was extracted with EA
  17. dry with materialthe combined organic extracts were dried over sodium chloride
  18. customdecanted
  19. customevaporated to dryness

Sources & evidence

ORD record
ord-6bcc19fbde4c4b1c9e58f306c2669624
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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