Pyridine → HCID 54142886, compound

HRID 1276676Notes

Reaction equation

HRID 1276676 reaction equation
[OH:1][CH:2]([C:15]1[C:24]([CH3:25])=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[CH3:26])[C:3]1[CH:8]=[C:7]([N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH:6]=[CH:5][C:4]=1[CH3:14].N1C=CC=CC=1.[CH3:33][C:34]1[CH:39]=[CH:38][C:37]([S:40]([NH:43][C@@H:44]([CH3:48])[C:45](Cl)=[O:46])(=[O:42])=[O:41])=[CH:36][CH:35]=1>ClC(Cl)C>[N:9]1([C:7]2[CH:6]=[CH:5][C:4]([CH3:14])=[C:3]([CH:8]=2)[CH:2]([C:15]2[C:16]([CH3:26])=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][C:24]=2[CH3:25])[O:1][C:45](=[O:46])[C@@H:44]([NH:43][S:40]([C:37]2[CH:38]=[CH:39][C:34]([CH3:33])=[CH:35][CH:36]=2)(=[O:42])=[O:41])[CH3:48])[CH:13]=[CH:12][N:11]=[CH:10]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10882640Methyl (+/-)-4-[alpha-hydroxy-5-(1-imidazolyl)-2-methylbenzyl]-3,5-dimethylbenzoateHCID 12924680HCID 12924680, compound

Product 1

HCID 54142886HCID 54142886, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

Methyl (±)-4-[α-hydroxy-5-(1-imidazolyl)-2-methylbenzyl]-3,5-dimethylbenzoate (35 g) was suspended in dichloroethane (350 ml) and pyridine (12 ml) and a solution of (S)-2-(4-methylbenzenesulfonylamino)propionyl chloride (31.4 g) in dichloroethane (70 ml) was added dropwise to the suspension over 10 minutes with stirring under ice-cooling. The mixture was stirred at room temperature for 4 hours, and the reaction mixture was washed successively with water, 5% citric acid, 5% potassium carbonate and water. The organic layer was separated and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 58 g of methyl (±)-4-[5-(1-imidazolyl)-2-methyl-α-{(S)-2-(4-methylbenzenesulfonylamino)propionyloxy}benzyl]-3,5-dimethylbenzoate as a pale-yellow oil. This was crystallized from ethyl acetate (120 ml) and isopropyl ether (480 ml), and the obtained crystals were recrystallized from ethyl acetate (50 ml) and isopropyl ether (100 ml) to give 20 g of methyl (S)-4-[5-(1-imidazolyl)-2-methyl-α-{(S)-2-(4-methylbenzenesulfonylamino)propionyloxy}benzyl]-3,5-dimethylbenzoate as white crystals, melting point 103-105° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 4 hours
  3. washthe reaction mixture was washed successively with water, 5% citric acid, 5% potassium carbonate and water
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b46f365a03674d5caa9d2c4ebe607fcc
Source dataset
uspto-grants-2000_12
Patent number
US06166221

Reaction notes

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