Hydrochloric Acid → 4-[(4E)-3-(4-Carboxybenzyl)-5-{2-[4-(2-oxopyrrolidin-1-yl)butoxy]phenyl}pent-4-en-1-yl]benzoic acid

HRID 1512230Notes

Reaction equation

HRID 1512230 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[CH:46]=[CH:45][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][N:39]2[CH2:43][CH2:42][CH2:41][C:40]2=[O:44])[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>O1CCOCC1.[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][N:39]2[CH2:43][CH2:42][CH2:41][C:40]2=[O:44])[CH2:14][CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)=[CH:45][CH:46]=1)([OH:7])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59437414Methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-{2-[4-(2-oxopyrrolidin-1-yl)butoxy]phenyl}pent-4-en-1-yl]benzoate

Product 1

HCID 594374214-[(4E)-3-(4-Carboxybenzyl)-5-{2-[4-(2-oxopyrrolidin-1-yl)butoxy]phenyl}pent-4-en-1-yl]benzoic acid

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

13.7 mg (325 μmol) of lithium hydroxide monohydrate are added to a solution of 19 mg (32.5 μmol) of methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-{2-[4-(2-oxopyrrolidin-1-yl)butoxy]-phenyl}pent-4-en-1-yl]benzoate (Example 36A) in 0.5 ml of dioxane and 0.5 ml of 2 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 1.8 mg (3.2 μmol, 10.0% 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-11cccc0c9ee1433eb2881163e7379c3a
Source dataset
uspto-grants-2012_07
Patent number
US08217063B2

Reaction notes

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