Water → HCID 178524892, compound

HRID 574663Notes

Reaction equation

HRID 574663 reaction equation
[CH:1]([NH:14][C:15]([C:17]1[C:18]([OH:25])=[N:19][C:20]([CH:23]=[O:24])=[N:21][CH:22]=1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[O-:27]Cl=O.[Na+]>CC(O)(C)C>[CH:1]([NH:14][C:15]([C:17]1[C:18]([OH:25])=[N:19][C:20]([C:23]([OH:27])=[O:24])=[N:21][CH:22]=1)=[O:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23668197Sodium ChloriteHCID 178519983HCID 178519983, compound2×

Product 1

HCID 178524892HCID 178524892, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of step G product (2-h, 0.7 g) in t-BuOH (35 mL) was added NaH2PO4.12H2O (0.6 g, 1.7 mmol) followed by H2O (6 mL) and NaClO2 (0.95 g, 10.5 mmol). After being allowed to stir at the ambient temperature overnight, the reaction mixture was evaporated under vacuum to remove t-BuOH, diluted with H2O, treated with aq. HCl to pH 2 and the solid was filtered and the cake was washed with water and dried under vacuum to afford compound 2-i as a crude (0.35 g), which was directly used for next step without further purification.

Workup

  1. customthe reaction mixture was evaporated under vacuum
  2. customto remove t-BuOH
  3. additiondiluted with H2O
  4. additiontreated with aq. HCl to pH 2
  5. filtrationthe solid was filtered
  6. washthe cake was washed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-4a5ab8c9ddce4e73afd16ef1f447db32
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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