Lithium Hydroxide → HCID 12148809, compound

HRID 498887Notes

Reaction equation

HRID 498887 reaction equation
O=C(NCCC)C(N[C:11]([C:13]1[O:14][C:15]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]3[C:26]([C:31]4[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=4)=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:24])=[CH:18][C:16]=2[CH:17]=1)=[O:12])C1C=CC=CC=1.[Li+].[OH-:46]>C1COCC1.CO.O>[F:38][C:37]([F:39])([F:40])[C:34]1[CH:33]=[CH:32][C:31]([C:26]2[C:25]([C:23]([NH:22][C:19]3[CH:18]=[CH:16][C:15]4[O:14][C:13]([C:11]([OH:12])=[O:46])=[CH:17][C:21]=4[CH:20]=3)=[O:24])=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:36][CH:35]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 22262715HCID 22262715, compound

Product 1

HCID 12148809HCID 12148809, compoundYield 123.6%

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-cd1c7de574104dfdb8da5e1234fd3cfe
Source dataset
uspto-grants-2005_09
Patent number
US06949572B2

Reaction notes

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