Ammonia → HCID 70098359, compound

HRID 370328Notes

Reaction equation

HRID 370328 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:21][OH:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](N1C=CN=C1)([N:25]1C=CN=C1)=[O:24].N.O>C1COCC1>[C:23]([O:22][CH2:21][C@H:12]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])(=[O:24])[NH2:25]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 54354500HCID 54354500, compound

Product 1

HCID 70098359HCID 70098359, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 100 mL flask equipped with magnetic stirrer, N-benzyloxycarbonyl-m-fluorophenylalaninol (0.007 mole, 2.12 g) was dissolved in 50 ml of THF and was added with 1,1'-carbonyl diimidazole (0.007 mol, 1.14 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 recrystallized in a solution mixture of n-hexane and diethyl ether, to produce 2.18 g of O-carbamoyl-N-benzyloxycarbonyl-m-fluorophenylalaninol: Yield 91%.

Workup

  1. customIn a 100 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 recrystallized in a solution mixture of n-hexane and diethyl ether

Sources & evidence

ORD record
ord-de1ac74d346342939268d862028c5467
Source dataset
uspto-grants-2000_10
Patent number
US06140532

Reaction notes

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