Hydrochloric Acid → HCID 70099518, compound

HRID 370329Notes

Reaction equation

HRID 370329 reaction equation
[C:1]([O:4][CH2:5][C@H:6]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])[NH:7]C(OC(C)(C)C)=O)(=[O:3])[NH2:2].[ClH:23].C(=O)([O-])[O-].[K+].[K+].CCOCC>C1COCC1>[ClH:23].[C:1]([O:4][CH2:5][C@H:6]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])[NH2:7])(=[O:3])[NH2:2]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 54572634HCID 54572634, compound

Product 1

HCID 70099518HCID 70099518, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 100 mL flask equipped with magnetic stirrer, O-carbamoyl-N-(t-butyloxycarbonyl)-o-fluorophenylalaninol obtained in Example I was dissolved in 40 ml of THF and was added with 20 ml of 6N aqueous hydrochloric acid solution. The reaction mixture was stirred at room temperature for 8 hours, followed by the neutralization with saturated aqueous potassium carbonate solution. Thereafter, the organic layer was extracted 3 times with dichloromethane, dried over magnesium sulfate and distilled in vacuo, to give a yellowish liquid. This, was dissolved in 30 ml of THF and added with anhydrous hydrochloric acid at 0° C., to obtain desirable white precipitates. To this was added 30 ml of anhydrous ether, with the aim of maximizing the precipitation. As a result, 1.22 g of the title compound was obtained: Yield 73%.

Workup

  1. customIn a 100 mL flask equipped with magnetic stirrer
  2. extractionThereafter, the organic layer was extracted 3 times with dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. distillationdistilled in vacuo
  5. customto give a yellowish liquid
  6. customto obtain desirable white precipitates
  7. customthe precipitation

Sources & evidence

ORD record
ord-44841c3689a84b9396f96cb29376edcb
Source dataset
uspto-grants-2000_10
Patent number
US06140532

Reaction notes

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