Hydrochloric Acid → HCID 11701634, compound

HRID 2079583Notes

Reaction equation

HRID 2079583 reaction equation
[C@@H:1]([C@@H:5]1[NH:6][C:7](=[O:20])[C:8]2[C:13](/[C:14]/1=[CH:15]/[C:16]([O:18]C)=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH2:3][CH3:4])[CH3:2].C1COCC1.O.[Li+].[OH-].Cl>O.C1COCC1>[C@@H:1]([C@@H:5]1[NH:6][C:7](=[O:20])[C:8]2[C:13](/[C:14]/1=[CH:15]/[C:16]([OH:18])=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH2:3][CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11673489HCID 11673489, compoundHCID 21881883Oxolane--water (1/1)

Product 1

HCID 11701634HCID 11701634, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7 (273 mg, 1.0 mmol) in a 1:1 mixture of THF—H2O (10 mL) at room temperature was added a solution of LiOH (83.9 mg, 2.0, mmol) in H2O (2 mL). The mixture was stirred at room temperature overnight, and was then acidified with 5% HCl to pH=2. THF was eliminated in vacuo and the aqueous phase was extracted with EtOAc (3×50 mL). The organic phases were washed with brine and dried over MgSO4. Once the solvent had been eliminated in vacuo the raw product was obtained, which was purified by recrystallisation of EtOAc/hexane to give the acid 8 (140 mg, 54% yield) as a white solid.

Workup

  1. extractionthe aqueous phase was extracted with EtOAc (3×50 mL)
  2. washThe organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. customwas obtained
  5. customwhich was purified by recrystallisation of EtOAc/hexane

Sources & evidence

ORD record
ord-ae18dfac8ff141da8f6684b3db4b94de
Source dataset
uspto-grants-2011_04
Patent number
US07932266B2

Reaction notes

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