Hydrochloric Acid → HCID 74018438, compound

HRID 1819502Notes

Reaction equation

HRID 1819502 reaction equation
C1COCC1.[OH-].[Na+].[F:8][C:9]1[CH:14]=[C:13]([C:15](=[O:38])[NH:16][C:17]2[S:18][C:19]3[CH2:29][CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]=4[CH2:30][CH2:31][CH:32]([O:36][CH3:37])[CH2:33][CH2:34][CH3:35])[C:20]=3[N:21]=2)[CH:12]=[C:11]([F:39])[C:10]=1[CH:40]=[C:41]([CH3:47])[C:42]([O:44]CC)=[O:43].Cl>CO>[F:39][C:11]1[CH:12]=[C:13]([C:15](=[O:38])[NH:16][C:17]2[S:18][C:19]3[CH2:29][CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]=4[CH2:30][CH2:31][CH:32]([O:36][CH3:37])[CH2:33][CH2:34][CH3:35])[C:20]=3[N:21]=2)[CH:14]=[C:9]([F:8])[C:10]=1[CH:40]=[C:41]([CH3:47])[C:42]([OH:44])=[O:43]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57887230HCID 57887230, compound

Product 1

HCID 74018438HCID 74018438, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of THF (40 mL), methanol (40 mL), and 2N sodium hydroxide aqueous solution (40 mL) of 3-{2,6-difluoro-4-[4,5-dihydro-6-(3-methyloxyhexyl)naphtho[1,2-d]thiazol-2-ylcarbamoyl]phenyl}-2-methylacrylic acid ethyl ester (8) (7.0 g), was stirred at room temperature for 3 h. The reaction mixture was acidified with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, and brine, dried over magnesium sulfate, and evaporated. The residue was recrystallized from ethyl acetate to obtain the compound (A1) 5.5 g.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9b4cf451ba80404580076f9bcce4842a
Source dataset
uspto-grants-2009_10
Patent number
US07601746B2

Reaction notes

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