Lithium Hydroxide → HCID 10007057, compound

HRID 1294375Notes

Reaction equation

HRID 1294375 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[CH:19]=[C:20]([C:24]4[CH:29]=[CH:28][C:27]([CH:30]5[O:34][C:33]([CH3:36])([CH3:35])[O:32][CH:31]5[C:37]([O:39]CC)=[O:38])=[CH:26][CH:25]=4)[CH:21]=[CH:22][CH:23]=3)[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.[Li+].[OH-]>C1COCC1.CO>[CH:1]1([NH:4][C:5]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[CH:19]=[C:20]([C:24]4[CH:29]=[CH:28][C:27]([CH:30]5[O:34][C:33]([CH3:36])([CH3:35])[O:32][CH:31]5[C:37]([OH:39])=[O:38])=[CH:26][CH:25]=4)[CH:21]=[CH:22][CH:23]=3)[CH:8]=2)=[O:6])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69157597HCID 69157597, compound

Product 1

HCID 10007057HCID 10007057, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ester from step 3 in THF-MeOH (1:1, 0.5M) was added LiOH (3 eq, 2M) and the mixture was stirred at 50° C. for 15 min. The organic solvent evaporated, aqueous was acidified with HCl 1N and the acid extracted with EtOAc (3×). The combined organic extract was washed with brine, dried and solvent evaporated, the residue triturated in hexane/ether then isolated by filtration to afford the title acid.

Workup

  1. customThe organic solvent evaporated
  2. extractionthe acid extracted with EtOAc (3×)
  3. extractionThe combined organic extract
  4. washwas washed with brine
  5. customdried
  6. customsolvent evaporated
  7. customthe residue triturated in hexane/ether
  8. customthen isolated by filtration

Sources & evidence

ORD record
ord-9540a271259246a3a3cb846f48d71f44
Source dataset
uspto-grants-2007_07
Patent number
US07238706B2

Reaction notes

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