Sulfamic Acid → HCID 86752077, compound

HRID 862358Notes

Reaction equation

HRID 862358 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[CH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH2:28][CH2:29][CH3:30])[CH:25]=2)[CH:20]([C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)[CH:19]1[C:40]([O-:42])=[O:41])=[O:2].[O-:43]Cl=O.[Na+:46].NS(O)(=O)=[O:49]>CC(O)(C)C.O>[Na+:46].[Na+:46].[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[CH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH2:28][CH2:29][CH3:30])[CH:25]=2)[CH:20]([C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)[CH:19]1[C:40]([O-:42])=[O:41])([OH:43])=[O:2].[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[CH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH2:28][CH2:29][CH3:30])[CH:25]=2)[CH:20]([C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)[CH:19]1[C:40]([O-:42])=[O:41])([OH:49])=[O:2]

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 86752078HCID 86752078, compound

Product 1

HCID 86752077HCID 86752077, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of Methyl (1RS, 2SR, 3RS)-3-[2-[(4-formylpyridin-3-yl)oxy]-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (128 mg, 0.24 mmol) in t-BuOH (10 mL) was added a solution of NaClO2 (34 mg, 0.28 mmol) and NH2SO3H (40 mg, 0.42 mmol) in water (6 mL). The reaction mixture was stirred at room temperature for 2 h and it was partitioned between water and ethyl acetate. The ethyl acetate extract was washed with water and brine and dried (Mg2SO4). The solvent was removed in vacuo. The residue was purified by flash column chromatography (silica gel, 25% ethyl acetate/hexanes containing 5% of acetic acid) to afford the title compound (90 mg, 69%).

Workup

  1. customit was partitioned between water and ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with water and brine
  4. dry with materialdried (Mg2SO4)
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by flash column chromatography (silica gel, 25% ethyl acetate/hexanes containing 5% of acetic acid)

Sources & evidence

ORD record
ord-1276bfedec094589bd83a5f567d409d0
Source dataset
uspto-grants-1998_02
Patent number
US05716984

Reaction notes

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