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

HRID 455625노트

반응식

HRID 455625 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 21966525Dioxane Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-afd4f1f069454a5f90b8cd2920ca173d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497264B2

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