Hydrochloric Acid → HCID 25028933, compound

HRID 1512225Notes

Reaction equation

HRID 1512225 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[CH:45]=[CH:44][C:11]([CH2:12][CH:13](/[CH:26]=[CH:27]/[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH2:35][CH2:36][CH2:37][N:38]2[CH2:42][CH2:41][O:40][C:39]2=[O:43])[CH2:14][CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)=[O:7].Cl>C1COCC1.O>[C:6]([C:8]1[CH:9]=[CH:10][C:11]([CH2:12][CH:13](/[CH:26]=[CH:27]/[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH2:35][CH2:36][CH2:37][N:38]2[CH2:42][CH2:41][O:40][C:39]2=[O:43])[CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:24][CH:25]=2)=[CH:44][CH:45]=1)([OH:7])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59437433HCID 59437433, compound

Product 1

HCID 25028933HCID 25028933, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

81.5 mg (1.94 mmol) of lithium hydroxide monohydrate are added to a solution of 370 mg (0.647 mmol) of methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-{2-[3-(2-oxo-1,3-oxazolidin-3-yl)-propoxy]phenyl}pent-4-en-1-yl]benzoate (Example 26A) in 2 ml of THF and 2 ml of water, and the mixture is stirred at room temperature for 18 h. The mixture is then adjusted to pH 2 using 1 M hydrochloric acid and extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate. After filtration, the solvent is removed to dryness and the crude product is purified by preparative HPLC. This gives 114 mg (0.210 mmol, 32.4% of theory) of the title compound as a colorless solid.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. filtrationAfter filtration
  4. customthe solvent is removed to dryness
  5. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-03f9466571e9491b8d831107f0fe5cfc
Source dataset
uspto-grants-2012_07
Patent number
US08217063B2

Reaction notes

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