Lithium Hydroxide → HCID 66842825, compound

HRID 2242400Notes

Reaction equation

HRID 2242400 reaction equation
C([O:3][C:4](=[O:38])[C@H:5]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:29]([O:30][CH3:31])=[CH:28][C:27]([CH2:32][O:33][CH2:34][CH3:35])=[CH:26][C:25]=2[O:36][CH3:37])=[CH:20][CH:19]=1)[NH:6][C:7](=[O:16])[C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])C.[Li+].[OH-]>C1COCC1.O>[Cl:14][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:15])[C:8]=1[C:7]([NH:6][C@H:5]([C:4]([OH:38])=[O:3])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25]([O:36][CH3:37])=[CH:26][C:27]([CH2:32][O:33][CH2:34][CH3:35])=[CH:28][C:29]=2[O:30][CH3:31])=[CH:20][CH:19]=1)=[O:16]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66843037HCID 66843037, compound

Product 1

HCID 66842825HCID 66842825, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
5 °C

Procedure

To a solution of the compound of Example 1 (207 mg) in THF/H2O (8 ml/2 ml) was added LiOH (30 mg) at 5° C. The mixture was stirred at 5° C. for 20 hours, quenched with 6N HCl (1 ml) and extracted with AcOEt. The organic layer was washed with H2O and brine, dried (MgSO4) and evaporated. The residue was recrystallized from a mixture of MeOH, diethyl ether and hexane to yield the title compound (147 mg). The compound of Example 2 (301 mg) was also hydrolyzed in a similar manner to give the title compound (238 mg) mp. 196-198° C.; IR (Nujol) 3300, 3270, 1705, 1651, 1462, 1126 cm−1; MS (ESI−Q1MS) m/z 530 (M−H).

Workup

  1. customquenched with 6N HCl (1 ml)
  2. extractionextracted with AcOEt
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was recrystallized from a mixture of MeOH, diethyl ether and hexane

Sources & evidence

ORD record
ord-6fd233ac571c4b85b78501b02660b20c
Source dataset
uspto-grants-2010_03
Patent number
US07671090B2

Reaction notes

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