Hydrochloric Acid → HCID 59384156, compound

HRID 1010605Notes

Reaction equation

HRID 1010605 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]3[CH:15]=[C:14]([C:16]([O:18]CC)=[O:17])[N:13]=[C:12]3[C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>O1CCCC1.O.CO>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]3[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[N:13]=[C:12]3[C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67297093HCID 67297093, compound

Product 1

HCID 59384156HCID 59384156, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.62 g (1.7 mmol) of the compound from Step B in 10 mL of tetrahydrofuran, 5 mL of water and 5 mL of methanol was added 0.80 mL (4.0 mmol) of 5.0 M NaOH solution. The reaction mixture was stirred at ambient temperature overnight. Hydrochloric acid (2.0 M) was then added to neutralize the reaction mixture. After removal of the organic solvents in vacuo, dichloromethane (20 mL) was added and the organic layer was separated. The aqueous layer was extracted with dichloromethane (10 mL), and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound as a yellow foam. LC/MS 337.3 (M+1).

Workup

  1. customAfter removal of the organic solvents in vacuo, dichloromethane (20 mL)
  2. additionwas added
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with dichloromethane (10 mL)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d1a92a08a5548c594ef443887b7078e
Source dataset
uspto-grants-2011_07
Patent number
US07977339B2

Reaction notes

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