Hydrochloric Acid → HCID 12043737, compound

HRID 842951Notes

Reaction equation

HRID 842951 reaction equation
[C:1]([C:3]1([C:15]2[C:24]3[O:23][CH2:22][CH2:21][O:20][C:19]=3[C:18]([O:25][CH3:26])=[CH:17][CH:16]=2)[CH2:8][CH2:7][C:6](=[CH:9][C:10]([O:12]CC)=[O:11])[CH2:5][CH2:4]1)#[N:2].[OH-].[Na+].Cl>C(O)C.C1COCC1>[C:1]([C:3]1([C:15]2[C:24]3[O:23][CH2:22][CH2:21][O:20][C:19]=3[C:18]([O:25][CH3:26])=[CH:17][CH:16]=2)[CH2:4][CH2:5][C:6](=[CH:9][C:10]([OH:12])=[O:11])[CH2:7][CH2:8]1)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 22616357HCID 22616357, compound

Product 1

HCID 12043737HCID 12043737, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of Compound 10 (0.31 g, 0.87 mmol) obtained in Example 10 in ethanol (3.1 mL) and THF (3.1 mL) was added a 2 mol/L aqueous solution of sodium hydroxide (0.65 mL, 1.3 mmol), the mixture was stirred at 70° C. for 1 hour, and then a 2 mol/L aqueous solution of sodium hydroxide (0.65 mL, 1.3 mmol) was further added, followed by stirring at 70° C. for 1 hour. 1 mol/L hydrochloric acid was added dropwise under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate, the solvent was evaporated in vacuo, and the residue was triturated with ethanol to give Compound 11 (0.23 g, 82%) as a white solid.

Workup

  1. stirringby stirring at 70° C. for 1 hour
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customthe residue was triturated with ethanol

Sources & evidence

ORD record
ord-29bc083a653649dbac93317e30b5c91a
Source dataset
uspto-grants-2002_04
Patent number
US06376535B2

Reaction notes

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