Water → HCID 11114441, compound

HRID 1108485Notes

Reaction equation

HRID 1108485 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].[CH3:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[CH:35]=[C:34]([C@H:39]([CH3:43])[C:40](Cl)=[O:41])[CH:33]=[CH:32]2.O>CN(C)C=O.N1C=CC=CC=1.C1(C)C=CC=CC=1>[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:40](=[O:41])[C@H:39]([C:34]2[CH:33]=[CH:32][C:31]3[C:36](=[CH:37][CH:38]=[C:29]([O:28][CH3:27])[CH:30]=3)[CH:35]=2)[CH3:43])[CH:13]=[CH:12][N:11]=[CH:10]1

Participants

7

Reactant 3

HCID 962WaterHCID 54916922-(6-Methoxynaphthalen-2-yl)propanoyl chlorideHCID 10882640Methyl (+/-)-4-[alpha-hydroxy-5-(1-imidazolyl)-2-methylbenzyl]-3,5-dimethylbenzoate

Product 1

HCID 11114441HCID 11114441, compoundYield 100.5%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl (±)-4-[α-hydroxy-5-(1-imidazolyl)-2-methylbenzyl]-3,5-dimethylbenzoate (70 g) was suspended in dimethylformamide (350 ml) and pyridine (23.7 ml), and a solution of (S)-2-(6-methoxy-2-naphthyl)propionyl chloride (59.7 g) in toluene (250 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 poured into water (1400 ml). The precipitated oily substance was extracted with toluene and washed successively with 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 113 g of methyl (±)-4-[5-(1-imidazolyl)-α-{(S)-2-(6-methoxy-2-naphthyl)propionyloxy}-2-methylbenzyl]-3,5-dimethylbenzoate as a pale-yellow oil. This was crystallized from ethyl acetate (330 ml) and isopropyl ether (1300 ml) and the obtained crystals were recrystallized from isopropyl alcohol (300 ml) to give 47 g of methyl (S)-4-[5-(1-imidazolyl)-α-{(S)-2-(6-methoxy-2-naphthyl)propionyloxy}-2-methylbenzyl]-3,5-dimethylbenzoate as white crystals, melting point 156-158° C., optical rotation [α]D24 +87.3° (c=1, chloroform).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 4 hours
  3. extractionThe precipitated oily substance was extracted with toluene
  4. washwashed successively with 5% citric acid, 5% potassium carbonate and water
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d91288b49aa44c10b91a7122758f2ba8
Source dataset
uspto-grants-2000_05
Patent number
US06066739

Reaction notes

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