Sodium Hydroxide → 122331-76-4

HRID 1276678Notes

Reaction equation

HRID 1276678 reaction equation
[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH3:42])=[C:10]([CH:41]=2)[C@H:11]([C:29]2[C:38]([CH3:39])=[CH:37][C:32]([C:33]([O:35]C)=[O:34])=[CH:31][C:30]=2[CH3:40])[O:12]C(=O)[C@H](C2C=CC3C(=CC=C(OC)C=3)C=2)C)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+]>CO>[OH:12][C@@H:11]([C:29]1[C:30]([CH3:40])=[CH:31][C:32]([C:33]([OH:35])=[O:34])=[CH:37][C:38]=1[CH3:39])[C:10]1[CH:41]=[C:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH:7]=[CH:8][C:9]=1[CH3:42]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15888205HCID 15888205, compound

Product 1

HCID 11589275122331-76-4Yield 85.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl (R)-4-[5-(1-imidazolyl)-α-{(S)-2-(6-methoxy-2-naphthyl)propionyloxy}-2-methylbenzyl]-3,5-dimethylbenzoate (35 g) obtained in Example 9 was suspended in methanol (280 ml) and an aqueous solution (70 ml) containing sodium hydroxide (6.2 g) was added, which was followed by sting at 60° C. for 2 hours. The reaction mixture was concentrated and to the residue were added dimethylformamide (210 ml) and water (210 ml), which was followed by neutralization with glacial acetic acid (17.5 ml). The precipitated crystals were collected by filtration, washed with water and acetone, and recrystallized from dimethylformamide to give 17.8 g of (R)-4-[α-hydroxy-5-(1-imidazolyl)-2-methylbenzyl]-3,5-dimethylbenzoic acid, melting point 286-288° C. (decomposition), optical rotation [α]D21 +260.5° (c=1.0, dimethylformamide).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated and to the residue
  3. additionwere added dimethylformamide (210 ml) and water (210 ml), which
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with water and acetone
  6. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-47533392dcde403b94e7763b59c8cfc1
Source dataset
uspto-grants-2000_12
Patent number
US06166221

Reaction notes

Loading…