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

HRID 1512229Notes

Reaction equation

HRID 1512229 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[CH:49]=[CH:48][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[CH2:45][CH2:44][CH2:43][N:42]([CH3:46])[C:41]2=[O:47])[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.[OH-].[Na+]>[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[CH2:45][CH2:44][CH2:43][N:42]([CH3:46])[C:41]2=[O:47])[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:48][CH:49]=1)([OH:7])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59437423Methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-(2-{[5-(3-methyl-2-oxotetrahydropyrimidin-1(2H)-yl)pentyl]oxy}phenyl)pent-4-en-1-yl]benzoate

Product 1

HCID 594374314-[(4E)-3-(4-Carboxybenzyl)-5-(2-{[5-(3-methyl-2-oxotetrahydropyrimidin-1(2H)-yl)pentyl]oxy}-phenyl)pent-4-en-1-yl]benzoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

31.5 mg (750 μmol) of lithium hydroxide monohydrate are added to a solution of 47 mg (160 μmol) of methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-(2-{[5-(3-methyl-2-oxotetrahydro-pyrimidin-1(2H)-yl)pentyl]oxy}phenyl)pent-4-en-1-yl]benzoate (Example 35A) in 1.0 ml of THF and 1.0 ml of 1 M aqueous sodium hydroxide solution, 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 4.2 mg (7.0 μmol, 9.4% 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-5b23048d9c8146439eccdb7d390ba2d6
Source dataset
uspto-grants-2012_07
Patent number
US08217063B2

Reaction notes

Loading…