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

HRID 1512224Notes

Reaction equation

HRID 1512224 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][N:38]2[CH2:43][CH2:42][O:41][CH2:40][C:39]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>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[CH2:43][CH2:42][O:41][CH2:40][C:39]2=[O:44])[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:45][CH:46]=1)([OH:7])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59437426Methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-{2-[3-(3-oxomorpholin-4-yl)propoxy]phenyl}pent-4-en-1-yl]benzoate

Product 1

HCID 594374324-[(4E)-3-(4-Carboxybenzyl)-5-{2-[3-(3-oxomorpholin-4-yl)propoxy]phenyl}pent-4-en-1-yl]-benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

66.6 mg (1.59 mmol) of lithium hydroxide monohydrate are added to a solution of 0.31 g (0.53 mmol) of methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-{2-[3-(3-oxomorpholin-4-yl)propoxy]phenyl}-pent-4-en-1-yl]benzoate (Example 23A) 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 89.5 mg (0.16 mmol, 30.3% 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-bc75caece25d43c786a6f2eeff412cad
Source dataset
uspto-grants-2012_07
Patent number
US08217063B2

Reaction notes

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