Hydrogen Peroxide → HCID 54214369, compound

HRID 1860048Notes

Reaction equation

C([C@@H]1COC(=O)N1[C:14](=[O:34])[C@H:15]([O:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=1)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)C1C=CC=CC=1.[OH-:35].[Li+].OO>>[OH:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][C@@H:15]([O:24][C:25]2[CH:26]=[CH:27][C:28]([CH:31]([CH3:32])[CH3:33])=[CH:29][CH:30]=2)[C:14]([OH:34])=[O:35])=[CH:22][CH:21]=1

Participants

Reactant 3

HCID 784Hydrogen Peroxide

HCID 3939Lithium Hydroxide

HCID 69878411HCID 69878411, compound

Product 1

HCID 54214369HCID 54214369, compound

Procedure

In a similar manner to that described in Reference example 29(e), a reaction was carried out using (R)-4-benzyl-3-[(R)-3-(4-hydroxyphenyl)-2-(4-isopropylphenoxy)propionyl]oxazolidine-2-one (3.78 g), which is the product of Reference example 30(d), aqueous lithium hydroxide solution (1N, 20.6 ml) and aqueous hydrogen peroxide solution (31%, 2.26 ml) and the reaction mixture was treated to afford (R)-3-(4-hydroxyphenyl)-2-(4-isopropylphenoxy)propionic acid (2.18 g) as a white powder. This acid (1.95 g) was reacted with oxalyl chloride (2.73 ml) and 2-trimethylsilylethanol (4.66 ml) and the reaction mixture was treated in a similar manner to that described Reference example 29(e) to afford the desired compound (2.26 g) as a colorless oil.

Workup

additionthe reaction mixture was treated

Sources & evidence

ORD record: ord-cb860e44ce664eeb910044261bd7df0a
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528525B1

Reaction notes

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