Hydrochloric Acid → 4-(3-pyridyloxymethyl)-2-phenylbenzoyl-L-alanine

HRID 2121167Notes

Reaction equation

HRID 2121167 reaction equation
C[O:2][C:3](=[O:29])[C@H:4]([CH3:28])[NH:5][C:6](=[O:27])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:9][C:8]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+].CO.Cl>C(OCC)(=O)C.O>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([NH:5][C@H:4]([C:3]([OH:29])=[O:2])[CH3:28])=[O:27])=[C:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:9]=2)[CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 69892498[4-(3-Pyridyloxymethyl)-2-phenylbenzoyl]alanine methyl ester

Product 1

HCID 536549204-(3-pyridyloxymethyl)-2-phenylbenzoyl-L-alanine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To approximately 0.3 mmol of [4-(3-pyridyloxymethyl)-2-phenylbenzoyl]alanine methyl ester, prepared as in Example 187D, was added 1 mL of 1.39M NaOH in 5:1 methanol: water. The mixture was heated to reflux for 20 minutes, then 1 mL of water, 1.4 mL of 1M aqueous HCl, and 5 mL of ethyl acetate were added sequentially. The biphasic mixture was stirred, then separated, and the aqueous layer was extracted with additional ethyl acetate (2×5 mL). The combined ethyl acetate layers were dried over magnesium sulfate, filtered, and concentrated to give 4-(3-pyridyloxymethyl)-2-phenylbenzoyl-L-alanine as a foam. 1H NMR (300 MHz, d6-DMSO) δ 1.11 (d, J=7.1 Hz, 3H), 4.14 (quintet, J=7.3 Hz, 1H), 5.21 (s, 2H), 7.22-7.45 (m, 1H), 8.10 (d, J=4.1 Hz, 1H), 8.29 (d, J=1.7 Hz, 1H), 8.46 (d, J=7.5 Hz, 1H), 12.42 (br s, 1H); MS (DCI) m/e 377 (M+H)+, 394 (M+NH)+. Anal calcd for C22H20N2O4.0.15HCl: C, 69.19; H, 5.32; N, 7.34. Found: C, 69.22; H, 5.01; N, 7.07.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 20 minutes
  3. customseparated
  4. extractionthe aqueous layer was extracted with additional ethyl acetate (2×5 mL)
  5. dry with materialThe combined ethyl acetate layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c135e21956ec4b84bdecc7d98fc7980f
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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