Hydrochloric Acid → HCID 44188436, compound

HRID 885315Notes

Reaction equation

HRID 885315 reaction equation
C([O:8][C:9](=[O:50])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:13]([O:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][C:27]=2[CH2:36][N:37]2[C@@H:41]([CH3:42])[C@@H:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[O:39][C:38]2=[O:49])[CH:12]=1)C1C=CC=CC=1.[OH-].[Li+].Cl>CO>[CH2:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][C:9]([OH:50])=[O:8])=[CH:12][C:13]=1[O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:28][C:27]=1[CH2:36][N:37]1[C@@H:41]([CH3:42])[C@@H:40]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[O:39][C:38]1=[O:49])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58237506HCID 58237506, compound

Product 1

HCID 44188436HCID 44188436, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To {4-benzyloxy-3-[2-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-trifluoromethyl-phenoxy]-phenyl}-acetic acid benzyl ester (0.05 g, 0.07 mmol) in MeOH (3 mL) was added 1N aqueous lithium hydroxide (1 mL), and the reaction was stirred at 65° C. overnight. The mixture was then acidified with 1N aqueous HCl, and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by preparative HPLC to give the desired product.

Workup

  1. extractionthe aqueous layer was extracted twice with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-f86afce78a5b44479148de922983e98a
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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