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

HRID 931618ノート

反応式

HRID 931618 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-0ca07ccd5d0c4a80bf5ad0fa4ce9aa55
出典データセット
uspto-grants-2016_03
特許番号
US09296759B2

反応ノート

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