Potassium Hydroxide → (S)-(9-amino-2-bromo-7-iodo-9H-xanthen-9-yl)methanol

HRID 455625ノート

反応式

HRID 455625 の反応式
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([I:16])=[CH:9][CH:10]=3)[C@:5]3([CH2:20][O:19]C(=O)[NH:17]3)[C:4]=2[CH:3]=1.[OH-].[K+]>CO.O1CCOCC1>[NH2:17][C@@:5]1([CH2:20][OH:19])[C:4]2[CH:3]=[C:2]([Br:1])[CH:15]=[CH:14][C:13]=2[O:12][C:11]2[C:6]1=[CH:7][C:8]([I:16])=[CH:9][CH:10]=2

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 67383335(S)-2'-bromo-7'-iodospiro[oxazolidine-4,9'-xanthen]-2-one

生成物 1

HCID 67383446(S)-(9-amino-2-bromo-7-iodo-9H-xanthen-9-yl)methanol収率 37%

試薬・触媒・溶媒 1

HCID 21966525Dioxane Methanol溶媒

実験手順

In a 350-mL resealable vessel, the (S)-2′-bromo-7′-iodospiro[oxazolidine-4,9′-xanthen]-2-one (11 g, 24.02 mmol) was dissolved in 1:1 MeOH-dioxane (160 mL). Aqueous KOH (5 M, 48.0 mL, 240 mmol) was added. The vessel was sealed and placed in a 105° C. oil bath. After 24 h, the reaction was concentrated to remove the MeOH and most of the dioxane. The residue was diluted with water (200 mL) and the aqueous phase was extracted with 5% MeOH-DCM (4×200 mL). The organics were combined, washed with dilute brine (35 mL), dried over sodium sulfate and concentrated. The residue was purified by chromatography (1.5% MeOH/DCM) to afford (S)-(9-amino-2-bromo-7-iodo-9H-xanthen-9-yl)methanol (3.84 g, 8.89 mmol).

後処理

  1. customThe vessel was sealed
  2. customplaced in a 105° C.
  3. concentrationthe reaction was concentrated
  4. customto remove the MeOH
  5. additionThe residue was diluted with water (200 mL)
  6. extractionthe aqueous phase was extracted with 5% MeOH-DCM (4×200 mL)
  7. washwashed with dilute brine (35 mL)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography (1.5% MeOH/DCM)

出典と根拠

ORDレコード
ord-afd4f1f069454a5f90b8cd2920ca173d
出典データセット
uspto-grants-2013_07
特許番号
US08497264B2

反応ノート

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