Sulfamic Acid → HCID 21963925, compound

HRID 2212388Notes

Reaction equation

HRID 2212388 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:28]3[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=3[F:35])[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([C:20]3[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=3)[CH:23]=[O:24])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.S(=O)(=O)([OH:38])N.Cl([O-])=O.[Na+]>ClCCl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:28]3[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=3[F:35])[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([C:20]3[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=3)[C:23]([OH:38])=[O:24])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 21964009HCID 21964009, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 21963925HCID 21963925, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the product from Example 151 (58 mg, 0.11 mmol) in dichloromethane (3 mL) and water (3 mL) at 0° C. was added sulfamic acid (44 mg, 0.44 mmol) and sodium chlorite (30 mg, 0.33 mmol). The reaction was allowed to attain room temperature with stirring over 3 hours, the layers separated and the aqueous layer extracted with further dichloromethane (5 mL). The combined organic layers were dried (MgSO4) and evaporated to leave a residue which was filtered through a plug of silica eluting with ether:dichloromethane:iso-hexane 1:1:3, then purified by column chromatography on silica eluting with ethyl acetate:dichloromethane 1:1 +1% acetic acid to afford the desired compound (40 mg).

Workup

  1. customto attain room temperature
  2. customthe layers separated
  3. extractionthe aqueous layer extracted with further dichloromethane (5 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customevaporated
  6. customto leave a residue which
  7. filtrationwas filtered through a plug of silica eluting with ether:dichloromethane:iso-hexane 1:1:3
  8. custompurified by column chromatography on silica eluting with ethyl acetate:dichloromethane 1:1 +1% acetic acid

Sources & evidence

ORD record
ord-e2b2b869ee50491991e6393f0ecf5b4a
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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