Water → HCID 86705051, compound

HRID 1427265Notes

Reaction equation

HRID 1427265 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:17]2[C:25]3[C:20](=[C:21]([N:26]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[S:27]([CH3:30])(=[O:29])=[O:28])[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)([CH2:15][CH3:16])[C:9]#[C:10][C:11]([O:13]C)=[O:12])=[CH:4][CH:3]=1.O.[Li+].[OH-]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:17]2[C:25]3[C:20](=[C:21]([N:26]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:36])[CH3:37])[S:27]([CH3:30])(=[O:29])=[O:28])[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)([CH2:15][CH3:16])[C:9]#[C:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 70562147HCID 70562147, compound

Product 1

HCID 86705051HCID 86705051, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound from step A (100 mg, 0.17 mmol, enantiomer A) in MeOH (5 mL) was added H2O (1 mL), LiOH (72 mg, 1.7 mmol). The mixture was stirred at RT overnight. After removing the organic solvent, the residue was dissolved with H2O (5 mL) and adjusted to pH=4 with 1M HCl, then extracted with ethyl acetate, and washed with brine (20 mL), dried over dry sodium sulfate, then filtered. The solvent was evaporated to give the title compound. LC/MS m/z=583.0 [M+Na]+.

Workup

  1. customAfter removing the organic solvent
  2. dissolutionthe residue was dissolved with H2O (5 mL)
  3. extractionextracted with ethyl acetate
  4. washwashed with brine (20 mL)
  5. dry with materialdried over dry sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6a9fc686ff7c494ab210d0e70aa5aeb5
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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