Lithium Hydroxide → HCID 23431235, compound

HRID 47801Notes

Reaction equation

HRID 47801 reaction equation
C[O:2][C:3](=[O:35])[CH:4]([O:32][CH2:33][CH3:34])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][N:14]([C:22]([CH:24]2[CH2:31][C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]2=3)=[O:23])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:8][CH:7]=1.[Li+].[OH-]>O1CCCC1>[C:30]12[CH2:31][CH:24]([C:22]([N:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:13][CH2:12][C:9]3[CH:8]=[CH:7][C:6]([CH2:5][CH:4]([O:32][CH2:33][CH3:34])[C:3]([OH:35])=[O:2])=[CH:11][CH:10]=3)=[O:23])[C:25]=1[CH:26]=[CH:27][CH:28]=[CH:29]2

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69883850HCID 69883850, compound

Product 1

HCID 23431235HCID 23431235, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4-{2-[(bicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonyl)-heptyl-amino]-ethyl}-phenyl)-2-ethoxy-propionic acid methyl ester (96 mg, 0.20 mmol) and 1 M LiOH (0.60 mmol, 0.60 mL) in tetrahydrofuran (3 mL) was allowed to stir at room temperature for 16 hours. 2 N HCL was then added until the solution had a pH<2. After dilution with twice its volume in water, the aqueous layer was extracted with diethyl ether (2×). The organic layers were combined, washed with 2 M HCl (2×), dried over anhydrous sodium sulfate, and concentrated to give 3-(4-{2-[(bicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonyl)-heptyl-amino]-ethyl}-phenyl)-2-ethoxy-propionic acid as a clear oil (56 mg, 60%).

Workup

  1. addition2 N HCL was then added until the solution
  2. extractionAfter dilution with twice its volume in water, the aqueous layer was extracted with diethyl ether (2×)
  3. washwashed with 2 M HCl (2×)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7c104e772d044370aebca3800fc75bca
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

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