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3-Hydroxypyridine → [4-(3-Pyridyloxymethyl)-2-phenylbenzoyl]methionine methyl ester

HRID 2121204
Notes
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Reaction equation

HRID 2121204 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[CH3:10][O:11][C:12](=[O:35])[C@H:13]([CH2:31][CH2:32][S:33][CH3:34])[NH:14][C:15](=[O:30])[C:16]1[CH:21]=[CH:20][C:19]([CH2:22]Br)=[CH:18][C:17]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH-].[Na+]>CN(C=O)C>[CH3:10][O:11][C:12](=[O:35])[C@H:13]([CH2:31][CH2:32][S:33][CH3:34])[NH:14][C:15](=[O:30])[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][O:3][C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)=[CH:18][C:17]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 79713-HydroxypyridineHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 54323738(4-Bromomethyl-2-phenylbenzoyl)methionine methyl ester

Product 1

HCID 53962378[4-(3-Pyridyloxymethyl)-2-phenylbenzoyl]methionine methyl esterYield 25.7%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
3×

Procedure

To a 0° C. suspension in DMF (2 mL) of sodium hydride (90% in mineral oil, 38 mg, 0.95 mmol) was added a solution of 3-hydroxypyridine (95 mg, 1.0 mmol) in DMF (2 mL) dropwise and the mixture was stirred for 0.5 hours. A solution of (4-bromomethyl-2-phenylbenzoyl)methionine methyl ester (218 mg, 0.5 mmol) in DMF (1 mL) was added and the reaction mixture was stirred for 18 hours. The reaction mixture was poured into aqueous 2N sodium hydroxide and the mixture was extracted with ethyl acetate (3×). The combined organic extracts were dried, filtered and concentrated in vacuo. Chromatography on silica gel (60% ethyl acetate-hexanes, then ethyl acetate) gave [4-(3-pyridyloxymethyl)-2-phenylbenzoyl]methionine methyl ester (58 mg). 1H NMR (300 MHz, DMSO-d6) δ 12.66 (bs, 1H), 8.58 (d, 1H), 8.38 (d, 1H), 8.17 (dd, 1H), 7.30-7.56 (m, 10H), 5.29 (s, 2H), 4.29 (ddd, 1H), 2.23 (m, 2H), 1.98 (s, 3H), 1.84 (m, 2H). MS (CI NH3) m/e 454 (M+NH4)+, 437 (M+H)+. Anal calcd for C24H24N2O4S (+0.41 H2O): C, 64.94; H, 5.64; N, 6.31. Found: C, 64.94; H, 5.35; N,S 6.14.

Workup

  1. stirringthe reaction mixture was stirred for 18 hours
  2. extractionthe mixture was extracted with ethyl acetate (3×)
  3. customThe combined organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29d4c57c898e47e7b82cf1869e29d5cd
Source dataset
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06693123B2

Reaction notes

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