Sulfamic Acid → HCID 21963964, compound

HRID 2212383Notes

Reaction equation

HRID 2212383 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[F:34])[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([C:20]3[O:24][C:23]([CH:25]=[O:26])=[CH:22][CH:21]=3)=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.S(=O)(=O)([OH:37])N.Cl([O-])=O.[Na+]>ClCCl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[F:34])[CH2:12][CH2:13][CH:14]([CH2:17][C:18]([C:20]3[O:24][C:23]([C:25]([OH:37])=[O:26])=[CH:22][CH:21]=3)=[O:19])[CH2:15][CH2:16]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 21963908HCID 21963908, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 21963964HCID 21963964, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Example 139 (29 mg, 0.057 mmol) in dichloromethane (2 mL) and water (1 mL) cooled to 0° C. was added sulfamic acid followed by sodium chlorite. The reaction was left to stir, warming to room temperature over 2.5 hours. The layers were separated and the aqueous layer extracted further with dichloromethane. The combined organic layers were dried (MgSO4) and evaporated to a cream foam, which was purified by column chromatography on silica (50% ethyl acetate/49% dichloromethane/1% acetic acid) to obtain a white solid (10 mg).

Workup

  1. waitThe reaction was left
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted further with dichloromethane
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customevaporated to a cream foam, which
  6. customwas purified by column chromatography on silica (50% ethyl acetate/49% dichloromethane/1% acetic acid)

Sources & evidence

ORD record
ord-ff948b217c404cdeb86252fc0c83d604
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

Loading…