tert-Butyl carbazate → HCID 59504820, compound

HRID 1517203Notes

Reaction equation

HRID 1517203 reaction equation
[C:1]([O:5][C:6]([NH:8][NH2:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:10]1[CH2:14][CH2:13][C:12](=O)[CH2:11]1>C(O)C>[O:10]1[CH2:14][CH2:13]/[C:12](=[N:9]\[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])/[CH2:11]1

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 5293923-Oxotetrahydrofuran

Product 1

HCID 59504820HCID 59504820, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of hydrazinecarboxylic acid tert-butyl ester (8.85 g, 67 mmol) in ethanol (30 mL) was added to a solution of dihydro-furan-3-one (5.78 g, 67 mmol) in ethanol (100 mL). This mixture was heated at reflux for 19 hours, then cooled to room temperature and concentrated under reduced pressure. The resulting crude mixture was partitioned between water (100 mL) and dichloromethane (100 mL). The aqueous layer was basified and extracted with dichloromethane (50 mL). The combined organic extracts were dried over magnesium sulphate, filtered, and evaporated under reduced pressure to give an oil (10.56 g, 79%). APCI MS m/z 201 [MH]+

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux for 19 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting crude mixture was partitioned between water (100 mL) and dichloromethane (100 mL)
  5. extractionextracted with dichloromethane (50 mL)
  6. dry with materialThe combined organic extracts were dried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-97aa5c1251604c718983b9a0b9a62961
Source dataset
uspto-grants-2012_07
Patent number
US08232269B2

Reaction notes

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