Hydrochloric Acid → HCID 5472506, compound

HRID 1585143Notes

Reaction equation

HRID 1585143 reaction equation
[C:1]([O:4][CH2:5][CH:6]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH:7]C(OC(C)(C)C)=O)(=[S:3])[NH2:2].[ClH:22].C(=O)([O-])[O-].[K+].[K+].C(OCC)C>C1COCC1>[ClH:22].[C:1]([O:4][CH2:5][CH:6]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH2:7])(=[S:3])[NH2:2]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 11197673HCID 11197673, compound

Product 1

HCID 5472506HCID 5472506, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 100 mL flask equipped with magnetic stirrer, O-thiocarbamoyl-N-(t-butyloxycarbonyl)-(DL)-phenylalaninol obtained in Example 1 was dissloved 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 obtained desirable white precipitates. To this was added 30 mL of anhydrous diethyl ether, with the aim of maximizing the precipitation. As a result, 1.32 g of the title compound was obtained: Yield 82%.

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 obtained desirable white precipitates
  7. customthe precipitation

Sources & evidence

ORD record
ord-3c6fca0ba5a3499597d52d2d6e9cd6a2
Source dataset
uspto-grants-1999_08
Patent number
US05935997

Reaction notes

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