Lithium Hydroxide → HCID 12148809, compound

HRID 2085887Notes

Reaction equation

HRID 2085887 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[C:18]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:16])=[CH:10][C:8]=2[CH:9]=1)=[O:4].[Li+].[OH-]>C1COCC1.CO.O>[F:32][C:29]([F:30])([F:31])[C:26]1[CH:25]=[CH:24][C:23]([C:18]2[C:17]([C:15]([NH:14][C:11]3[CH:12]=[CH:13][C:7]4[O:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][C:8]=4[CH:10]=3)=[O:16])=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:28][CH:27]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 12148808HCID 12148808, compound

Product 1

HCID 12148809HCID 12148809, compoundYield 90.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product from step (c) (8.1 g) was dissolved in THF (100 mL) and methanol (100 mL). Under stirring conditions was added LiOH (2 g) in water (100 mL). The reaction mixture was stirred at room temperature for 30 minutes. The reaction solution was then concentrated in vacuo, acidified by adding 1 N HCl solution. The product was extracted with ether (2×300 mL), and combined organic layers were washed with brine (2×50 mL) and then dried over MgSO4. The organic layer was then concentrated in vacuo to give the crude product which was purified by recrystallization from ether/hexane to give 7.1 g of the title compound.

Workup

  1. concentrationThe reaction solution was then concentrated in vacuo
  2. additionby adding 1 N HCl solution
  3. extractionThe product was extracted with ether (2×300 mL)
  4. washwere washed with brine (2×50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationThe organic layer was then concentrated in vacuo
  7. customto give the crude product which
  8. customwas purified by recrystallization from ether/hexane

Sources & evidence

ORD record
ord-b8e6237ff4fa4f2baaa75e652d5a6e38
Source dataset
uspto-grants-2004_04
Patent number
US06720351B2

Reaction notes

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