Sodium Hydroxide → 122331-77-5
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
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Methyl (S)-4-[5-(1-imidazolyl)-α-{(S)-2-(6-methoxy-2-naphthyl)propionyloxy}-2-methylbenzyl]-3,5-dimethylbenzoate (47 g) obtained in Example 1 was suspended in methanol (376 ml) and an aqueous solution (95 ml) containing sodium hydroxide (8 g) was added, which was followed by stirring at 60° C. for 2 hours. The reaction mixture was concentrated and to the residue were added dimethylformamide (300 ml) and water (300 ml), which was followed by neutralization with glacial acetic acid (23 ml). The precipitated crystals were collected by filtration, washed with water and acetone, and recrystallized from dimethylformamide to give 25.3 g of (S)-4-[α-hydroxy-5-(1-imidazolyl)-2-methylbenzyl]-3,5-dimethylbenzoic acid, melting point 286-288° C. (decomposition), optical rotation [α]D21 -261.5° (c=1.0, dimethylformamide).
Workup
- additionwas added
- concentrationThe reaction mixture was concentrated and to the residue
- additionwere added dimethylformamide (300 ml) and water (300 ml), which
- filtrationThe precipitated crystals were collected by filtration
- washwashed with water and acetone
- customrecrystallized from dimethylformamide
Sources & evidence
- ORD record
- ord-eb777894d51447458c91da73d595a2f4
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06166221
Reaction notes
Loading…