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

HRID 1512226Notes

Reaction equation

HRID 1512226 reaction equation
O.[OH-].[Li+].[F:4][C:5]1[CH:6]=[CH:7][C:8]([O:37][CH2:38][CH2:39][CH2:40][N:41]2[CH2:45][CH2:44][CH2:43][C:42]2=[O:46])=[C:9](/[CH:11]=[CH:12]/[CH:13]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([O:35]C)=[O:34])=[CH:29][CH:28]=2)[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]=1.Cl>C1COCC1.O>[C:33]([C:30]1[CH:29]=[CH:28][C:27]([CH2:26][CH:13](/[CH:12]=[CH:11]/[C:9]2[CH:10]=[C:5]([F:4])[CH:6]=[CH:7][C:8]=2[O:37][CH2:38][CH2:39][CH2:40][N:41]2[CH2:45][CH2:44][CH2:43][C:42]2=[O:46])[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:32][CH:31]=1)([OH:35])=[O:34]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59437427Methyl 4-{(4E)-5-{5-fluoro-2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}-3-[4-(methoxy-carbonyl)benzyl]pent-4-en-1-yl}benzoate

Product 1

HCID 250289344-[(4E)-3-(4-Carboxybenzyl)-5-{5-fluoro-2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}pent-4-en-1-yl]benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.57 mg (61.3 mmol) of lithium hydroxide monohydrate are added to a solution of 12 mg (10.4 μmol) of methyl 4-{(4E)-5-{5-fluoro-2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}-3-[4-(methoxy-carbonyl)benzyl]pent-4-en-1-yl}benzoate (Example 29A) in 0.3 ml of THF and 0.3 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 5.0 mg (8.93 μmol, 43.8% 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-4b4979062cac4f54a4ed90434d99211f
Source dataset
uspto-grants-2012_07
Patent number
US08217063B2

Reaction notes

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