Water → HCID 22179504, compound

HRID 1796685Notes

Reaction equation

HRID 1796685 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:41])=[C:8]2[C:13]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][C:29]([C:32](=[O:37])[NH:33][CH2:34][CH2:35][OH:36])([CH3:31])[CH3:30])=[CH:17][CH:16]=3)=[C:12]([C:38]#[N:39])[CH:11]=[N:10][N:9]2[CH:40]=1)=[O:5])C.[OH-].[Na+].O>CCO>[C:38]([C:12]1[CH:11]=[N:10][N:9]2[CH:40]=[C:6]([C:4]([OH:5])=[O:3])[C:7]([CH3:41])=[C:8]2[C:13]=1[NH:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][C:29]([C:32](=[O:37])[NH:33][CH2:34][CH2:35][OH:36])([CH3:31])[CH3:30])=[CH:19][CH:20]=1)#[N:39]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21025115HCID 21025115, compound

Product 1

HCID 22179504HCID 22179504, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 433E (180 mg, 0.323 mmol) and 1N NaOH (0.68 ml, 0.68 mmol) in EtOH (4 ml) was heated to reflux for 2 days, cooled to rt. Removal of the solvent in vacuo gave a gray oil. Treated with H2O (4 ml), the aqueous solution was washed with EtOAc (3×2 ml) and added to a mixture of 6N HCl (1.5 ml) and brine (5 ml). The resulting suspension was cooled to 0° C. and filtered, dried in vacuo to gave 433F (171 mg, 96%) as a dim dark solid. It has a retention time of 5.31 min (standard LC1 method, 8 min run). MS Found: (M+H)+=530.0

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 days
  3. customRemoval of the solvent in vacuo
  4. customgave a gray oil
  5. washthe aqueous solution was washed with EtOAc (3×2 ml)
  6. additionadded to a mixture of 6N HCl (1.5 ml) and brine (5 ml)
  7. temperatureThe resulting suspension was cooled to 0° C.
  8. filtrationfiltered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-841545a5c0b8478dbf793b31ac92208a
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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