Sulfamic Acid → HCID 10208859, compound

HRID 862348Notes

Reaction equation

HRID 862348 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[CH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH2:25][CH3:26])[CH:21]=2)[CH:16]([C:27]2[CH:32]=[CH:31][C:30]3[O:33][CH2:34][O:35][C:29]=3[CH:28]=2)[CH:15]1[C:36]([OH:38])=[O:37].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:41].Cl([O-])=O.[Na+].S(=O)(=O)(O)N>ClCCl.O>[C:2]([CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[CH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH2:25][CH3:26])[CH:21]=2)[CH:16]([C:27]2[CH:32]=[CH:31][C:30]3[O:33][CH2:34][O:35][C:29]=3[CH:28]=2)[CH:15]1[C:36]([OH:38])=[O:37])([OH:41])=[O:1]

Participants

7

Reactant 4

HCID 5987Sulfamic AcidHCID 159087TriacetoxyperiodinaneHCID 18427642HCID 18427642, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 10208859HCID 10208859, compoundYield 17.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

(1RS, 2SR, 3RS)-3-[2-(3-Hydroxyprop-1-yloxy)-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid (0.07 g, 0.13 mmol) was dissolved in dry dichloromethane (0.5 ml) and Dess-Martin periodinane (0.07 g, 0.17 mmol) added in dry dichloromethane (1 ml). After 2h. the product was partitioned between ether and saturated aqueous sodium carbonate solution containing sodium thiosulfate. The ether extract was washed with water then brine, dried (MgSO4 anhydrous), filtered and evaporated to give an oil which was used without purification. The crude product was dissolved in t-butanol (5 ml) and to this was added a solution of sodium chlorite (1 8 mg, 0.2 mmol) and sulfamic acid (21 mg, 0.22 mmol) in water (1.5 ml). After 1 h. stirring at ambient temperature the product was extracted into ethyl acetate. The organic layer was washed with water then brine then dried (MgSO4 anhyd.) filtered and evaporated to give an oil. The product was purified by column chromatography on silica-gel (eluant: ethyl acetate/hexane/3% acetic acid) to give 12 mg of free acid which was converted to its bis-dicyclohexylamine salt.

Workup

  1. customAfter 2h. the product was partitioned between ether and saturated aqueous sodium carbonate solution
  2. additioncontaining sodium thiosulfate
  3. extractionThe ether extract
  4. washwas washed with water
  5. dry with materialbrine, dried (MgSO4 anhydrous)
  6. filtrationfiltered
  7. customevaporated
  8. customto give an oil which
  9. customwas used without purification
  10. dissolutionThe crude product was dissolved in t-butanol (5 ml)
  11. extractionwas extracted into ethyl acetate
  12. washThe organic layer was washed with water
  13. dry with materialbrine then dried (MgSO4 anhyd.)
  14. filtrationfiltered
  15. customevaporated
  16. customto give an oil
  17. customThe product was purified by column chromatography on silica-gel (eluant: ethyl acetate/hexane/3% acetic acid)

Sources & evidence

ORD record
ord-2fecf8fa81cf4fe983890aa082f03edc
Source dataset
uspto-grants-1998_02
Patent number
US05716984

Reaction notes

Loading…