Hydrochloric Acid → (3R)-3-(3-Isoxazolyl)-3-(3-((phenylmethyl)oxy)phenyl)propanoic acid

HRID 1662573ノート

反応式

HRID 1662573 の反応式
[O:1]1[CH:5]=[CH:4][C:3]([C@@H:6]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:24]=2)[CH2:7][C:8](N2[C@H](CC3C=CC=CC=3)COC2=O)=[O:9])=[N:2]1.[OH:37]O.[Li+].[OH-].Cl>C1COCC1.O>[O:1]1[CH:5]=[CH:4][C:3]([C@@H:6]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:24]=2)[CH2:7][C:8]([OH:9])=[O:37])=[N:2]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 57706758(4R)-3-((3R)-3-(3-Isoxazolyl)-3-(3-((phenylmethyl)oxy)phenyl)propanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one

生成物 1

HCID 57706884(3R)-3-(3-Isoxazolyl)-3-(3-((phenylmethyl)oxy)phenyl)propanoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of (R)-4-benzyl-3-((R)-3-(3-(benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one (94.1C) (0.558 g, 1.16 mmol) in THF (12 mL) was cooled to 0° C. H2O2 (30% w/w, 0.50 mL) was added, and was followed by addition of LiOH, monohydrate (0.0643 mL, 2.31 mmol) in water (4 mL). The resulting mixture was stirred at 0° C. for 2 hours. The organic solvent was blown away by nitrogen, and the aqueous mixture was acidified with 1N HCl to pH 3-5. The mixture was extracted with EtOAc (100 mL). The organic phase was washed with brine, dried over anhydrous Na2SO4. After removing solvent, crude product (94.1D) (491 mg) was obtained.

後処理

  1. extractionThe mixture was extracted with EtOAc (100 mL)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customAfter removing solvent

出典と根拠

ORDレコード
ord-0e6d1673694d4a1393e44a481bc19fb3
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

反応ノート

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