Hydrochloric Acid → 4-[(4E)-3-(4-Carboxybenzyl)-5-(2-{[5-(2-oxo-1,3-oxazolidin-3-yl)pentyl]oxy}phenyl)pent-4-en-1-yl]benzoic acid

HRID 1512228Notes

Reaction equation

HRID 1512228 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[CH:47]=[CH:46][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][CH2:38][CH2:39][N:40]2[CH2:44][CH2:43][O:42][C:41]2=[O:45])[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][CH2:38][CH2:39][N:40]2[CH2:44][CH2:43][O:42][C:41]2=[O:45])[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:46][CH:47]=1)([OH:7])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59437425Methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-(2-{[5-(2-oxo-1,3-oxazolidin-3-yl)pentyl]oxy}-phenyl)pent-4-en-1-yl]benzoate

Product 1

HCID 594374164-[(4E)-3-(4-Carboxybenzyl)-5-(2-{[5-(2-oxo-1,3-oxazolidin-3-yl)pentyl]oxy}phenyl)pent-4-en-1-yl]benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

8.75 mg (208 mmol) of lithium hydroxide monohydrate are added to a solution of 25 mg (41.7 μmol) of methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-(2-{[5-(2-oxo-1,3-oxazolidin-3-yl)-pentyl]oxy}phenyl)pent-4-en-1-yl]benzoate (Example 33A) in 0.5 ml of THF and 0.5 ml of water, and the mixture is stirred at room temperature for 16 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, filtered and concentrated. The residue obtained is purified by preparative HPLC. This gives 1.5 mg (2.62 μmol, 6.3% of theory) of the title compound.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue obtained
  6. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-ad11ae3292d04e5e9a132af1a4f0af2b
Source dataset
uspto-grants-2012_07
Patent number
US08217063B2

Reaction notes

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