Sodium Hydroxide → HCID 11486771, compound

HRID 2219701Notes

Reaction equation

HRID 2219701 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]2[C:17](=[O:18])[CH2:16][CH2:15][CH:14]2[CH2:19][CH2:20][CH:21]([OH:30])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[F:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][CH:21]([OH:30])[CH2:20][CH2:19][CH:14]2[CH2:15][CH2:16][C:17](=[O:18])[N:13]2[CH2:12][CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:31])=[O:2])=[CH:5][CH:6]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69270428HCID 69270428, compound

Product 1

HCID 11486771HCID 11486771, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Analogous to the procedure described for Compound 1A, Step F, 4-(3-{2-[4-(4-fluoro-phenyl)-3-hydroxy-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzoic acid methyl ester (61.1 mg, 0.143 mmol) was hydrolyzed with 6N NaOH (1 mL) in MeOH (5 mL) at room temperature over 24 h. Purification by medium pressure chromatography eluting with a solvent gradient (CH2Cl2 to 2% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2 to 6% MeOH in CH2Cl2 to 10% MeOH in CH2Cl2) provided the title compound (45 mg). 1H NMR (CDCl3) δ 7.97 (d, 2H), 7.25 (m, 2H), 7.14 (m, 2H), 6.99 (m, 2H), 3.75-3.58 (m, 3H), 2.97 (m, 1H), 2.69 (m, 4H), 2.40 (m, 2H), 2.15-1.35 (m, 9H); MS 413.8 (M+).

Workup

  1. customPurification by medium pressure chromatography
  2. washeluting with a solvent gradient (CH2Cl2 to 2% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2 to 6% MeOH in CH2Cl2 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-02d783b1b0eb4bb9bfeaf203a7d30618
Source dataset
uspto-grants-2008_08
Patent number
US07414071B2

Reaction notes

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