Methanol → HCID 178507416, compound

HRID 44448Notes

Reaction equation

HRID 44448 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C@@H:15]3[CH2:19][CH2:18][CH2:17][N:16]3[C:20](=[O:28])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.CO.O1CCCC1.[Cl-].[NH4+]>O.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C@@H:15]3[CH2:19][CH2:18][CH2:17][N:16]3[C:20](=[O:28])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:13][CH:14]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 178520215HCID 178520215, compound

Product 1

HCID 178507416HCID 178507416, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of the Product from Example 1I (0.137 g, 0.36 mmol) in a mixture of water (0.75 mL), methanol (1.5 mL) and tetrahydrofuran (1.5 mL) was added iron (0.102 g, 1.82 mmol) and ammonium chloride (0.030 g, 0.54 mmol) and the resulting mixture was heated with vigorous stirred at 75° C. for one hour. The warm reaction mixture was filtered through celite and rinsed well with methanol and tetrahydrofuran. The filtrate was concentrated and partitioned between 10% NaHCO3 solution and ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated to give a waxy solid that was used without purification (97%).

Workup

  1. temperaturethe resulting mixture was heated
  2. customThe warm reaction mixture
  3. filtrationwas filtered through celite
  4. washrinsed well with methanol and tetrahydrofuran
  5. concentrationThe filtrate was concentrated
  6. custompartitioned between 10% NaHCO3 solution and ethyl acetate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a waxy solid that
  11. customwas used without purification (97%)

Sources & evidence

ORD record
ord-6f899b35a50b4ffc8224bdc0516decff
Source dataset
uspto-grants-2013_09
Patent number
US08541424B2

Reaction notes

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