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Sodium Hydroxide → HCID 25183514, compound

HRID 1925744
Notes
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Reaction equation

HRID 1925744 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([S:10]([NH:13][C:14]3[CH:18]=[CH:17][S:16][C:15]=3[C:19]([O:21]C)=[O:20])(=[O:12])=[O:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>O1CCCC1.CO>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([S:10]([NH:13][C:14]3[CH:18]=[CH:17][S:16][C:15]=3[C:19]([OH:21])=[O:20])(=[O:11])=[O:12])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 8823202HCID 8823202, compound

Product 1

HCID 25183514HCID 25183514, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 125 (0.30 g; 0.89 mmol) in tetrahydrofuran (20 mL) and methanol (7 mL) was added aqueous sodium hydroxide (20 mL; 2N) and then heated at 80° C. for 16 hours. The reaction mixture was allowed to cool to room temperature and then extracted with diethyl ether (20 mL). The aqueous layer was separated and acidified with aqueous hydrochloric acid (15 mL; 2N) then extracted with ethyl acetate (2×20 mL). The combined organic phases were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield the title product as an off-white solid (0.29 g).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with diethyl ether (20 mL)
  3. customThe aqueous layer was separated
  4. extractionthen extracted with ethyl acetate (2×20 mL)
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-566b62d6d89b4df58f60af43eadb1342
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178699B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes