Lithium Hydroxide → HCID 44205945, compound

HRID 456222Notes

Reaction equation

HRID 456222 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][C:6]1[CH:7]=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=2[CH2:25][N:26]2[C@@H:30]([CH3:31])[C@@H:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[O:28][C:27]2=[O:38])[C:9]([O:12][CH2:13][CH3:14])=[CH:10][CH:11]=1)C.[OH-].[Li+]>CO>[CH2:13]([O:12][C:9]1[C:8]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][C:16]=2[CH2:25][N:26]2[C@@H:30]([CH3:31])[C@@H:29]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[O:28][C:27]2=[O:38])=[CH:7][C:6]([CH2:5][C:4]([OH:39])=[O:3])=[CH:11][CH:10]=1)[CH3:14]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66892231HCID 66892231, compound

Product 1

HCID 44205945HCID 44205945, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To [6-ethoxy-2′-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid ethyl ester (0.18 mmol) in MeOH (3 mL) was added aqueous lithium hydroxide (1N; 1 mL), and the reaction was stirred overnight at 70° C. After acidification with 1N aqueous HCl, the aqueous layer was separated and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the crude material was purified by preparative HPLC to give the desired product. M+H is 514.

Workup

  1. customAfter acidification with 1N aqueous HCl, the aqueous layer was separated
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-9c8ec4d705874edc98c6bcb06d52b2a2
Source dataset
uspto-grants-2013_07
Patent number
US08497381B2

Reaction notes

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