Sodium Hydroxide → 4-{2-[2-(3-Hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-ethoxy}-benzoic acid

HRID 2219704Notes

Reaction equation

HRID 2219704 reaction equation
C([Si](C)(C)OC(CC1C=CC=CC=1)CCC1NC(=O)CC1)(C)(C)C.C([O:27][C:28](=[O:55])[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][N:38]2[C:42](=[O:43])[CH2:41][CH2:40][CH:39]2[CH2:44][CH2:45][CH:46]([OH:54])[CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:31][CH:30]=1)C.[OH-].[Na+]>>[OH:54][CH:46]([CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH2:45][CH2:44][CH:39]1[CH2:40][CH2:41][C:42](=[O:43])[N:38]1[CH2:37][CH2:36][O:35][C:32]1[CH:33]=[CH:34][C:29]([C:28]([OH:55])=[O:27])=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 129700855-[3-(Tert-butyl-dimethyl-silanyloxy)-4-phenyl-butyl]-pyrrolidin-2-oneHCID 692703774-{2-[2-(3-Hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-ethoxy}-benzoic acid ethyl ester

Product 1

HCID 111654074-{2-[2-(3-Hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-ethoxy}-benzoic acidYield 85.6%

Procedure

Analogous to the procedure described for Compound 1A, Step F, 4-{2-[2-(3-hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-ethoxy}-benzoic acid ethyl ester (52 mg, 0.122 mmol) was hydrolyzed with 6N NaOH (1 mL) to yield the title compound (41.5 mg). 1H NMR (CDCl3) δ 7.98 (d, 2H), 7.32-7.16 (m, 5H), 6.85 (m, 2H), 4.13 (m, 2H), 3.92 (m, 1H), 3.81 (m, 1H), 3.75 (m, 1H), 3.40 (m, 1H), 2.82 (m, 1H), 2.66 (m, 1H), 2.36 (m, 2H), 2.10 (m, 2H), 1.70-1.34 (m, 5H); MS 398.4 (M+1), 396.3 (M−1).

Sources & evidence

ORD record
ord-94187eaa11514906ad0ff32a468b1bec
Source dataset
uspto-grants-2008_08
Patent number
US07414071B2

Reaction notes

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