Hydrochloric Acid → HCID 117700766, compound

HRID 873531Notes

Reaction equation

HRID 873531 reaction equation
O.[OH-].[Li+].[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[C:16]([C:18]([O:20]C)=[O:19])[C:15]([C:22]#[C:23][Si](C)(C)C)=[CH:14][CH:13]=2)=[C:8]([CH3:28])[C:7]=1[CH:29]1[C:42]2[C:41](=[O:43])[CH2:40][C:39]([CH3:45])([CH3:44])[CH2:38][C:37]=2[O:36][C:35]2[CH2:34][C:33]([CH3:47])([CH3:46])[CH2:32][C:31](=[O:48])[C:30]1=2.Cl>C1COCC1.O>[C:22]([C:15]1[C:16]([C:18]([OH:20])=[O:19])=[N:17][C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH3:4])=[C:7]([CH:29]3[C:30]4[C:31](=[O:48])[CH2:32][C:33]([CH3:46])([CH3:47])[CH2:34][C:35]=4[O:36][C:37]4[CH2:38][C:39]([CH3:44])([CH3:45])[CH2:40][C:41](=[O:43])[C:42]3=4)[C:8]=2[CH3:28])=[CH:13][CH:14]=1)#[CH:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 131732564HCID 131732564, compound

Product 1

HCID 117700766HCID 117700766, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (303 mg, 7.21 mmol) was added to a solution of the methyl 6-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]-3-[(trimethylsilyl)ethynyl]pyridine-2-carboxylate produced in Example 12-2 (564 mg, 0.90 mmol) in THF (11 ml) and water (5.5 ml) at room temperature, and the mixture thus obtained was then stirred at the same temperature as above for 17 hours. Thereafter, a 1 N aqueous solution of hydrochloric acid (7.21 ml) was added to the reaction solution, and water was then added thereto. The solution thus mixed was then extracted with dichloromethane. The organic layer thus obtained was dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the solid thus obtained was then washed with a mixed solution of diethyl ether and hexane, followed by collection by filtration and drying, to obtain the title compound (435 mg, yield: 89%).

Workup

  1. customthe mixture thus obtained
  2. additionwas then added
  3. additionThe solution thus mixed
  4. extractionwas then extracted with dichloromethane
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled away under reduced pressure
  8. customthe solid thus obtained
  9. washwas then washed with a mixed solution of diethyl ether and hexane
  10. filtrationfollowed by collection by filtration
  11. customdrying

Sources & evidence

ORD record
ord-97a1b530f007457ca7fc6a467871f496
Source dataset
uspto-grants-2015_03
Patent number
US08975263B2

Reaction notes

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