Ammonia → HCID 54572634, compound

HRID 1292593Notes

Reaction equation

HRID 1292593 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:18][OH:19])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:20](N1C=CN=C1)([N:22]1C=CN=C1)=[O:21].N.O>C1COCC1>[C:20]([O:19][CH2:18][C@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])[NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])(=[O:21])[NH2:22]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 18660294HCID 18660294, compound

Product 1

HCID 54572634HCID 54572634, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 250 mL flask equipped with magnetic stirrer, N-(t-butyloxycarbonyl)-o-fluorophenylalaninol (0.096 mole, 2.15 g) was dissolved in 200 ml of THF and was added with 1,1'-carbonyldiimidazole (0.010 mol, 1.62 g) at 0° C. The reaction mixture was stirred at room temperature for 2 hours, followed by the injection of ammonia at 0° C. for 30 min. Following elevating to room temperature, water was added to terminate the reaction. The organic layer was extracted 3 times with dichloromethane, dried over magnesium sulfate and distilled in vacuo, to give a solid. This was recrystalized in a solution mixture of n-hexane and diethyl ether, to produce 1.93 g of O-carbamoyl-N-(t-butyloxycarbonyl)-o-fluorophenylalaninol: Yield 75%.

Workup

  1. customIn a 250 mL flask equipped with magnetic stirrer
  2. customto room temperature
  3. customto terminate
  4. customthe reaction
  5. extractionThe organic layer was extracted 3 times with dichloromethane
  6. dry with materialdried over magnesium sulfate
  7. distillationdistilled in vacuo
  8. customto give a solid
  9. customThis was recrystalized in a solution mixture of n-hexane and diethyl ether

Sources & evidence

ORD record
ord-55e862a8398e4d90970d0edca457e3c7
Source dataset
uspto-grants-1998_05
Patent number
US05756817

Reaction notes

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