Bromine → 5-bromo-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

HRID 2057584노트

반응식

HRID 2057584 반응식
C([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11]C(=O)C2C=CC=CC=2)[O:8][C@@H:7]([N:20]2[CH:27]=[CH:26][C:24](=[O:25])[NH:23][C:21]2=[O:22])[C@H:6]1[F:28])(=O)C.C([O-])(=O)C.[Na+].[Br:34]Br>C(O)(=O)C>[F:28][C@H:6]1[C@H:5]([OH:4])[C@@H:9]([CH2:10][OH:11])[O:8][C@H:7]1[N:20]1[CH:27]=[C:26]([Br:34])[C:24](=[O:25])[NH:23][C:21]1=[O:22]

참가 물질

5

반응물 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 70466634HCID 70466634, 화합물

생성물 1

HCID 52713805-bromo-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione수율 78.4%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

To a solution of 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil (500 mg) and sodium acetate (100 mg) in 5 ml of glacial acetic acid is added a solution of bromine (240 mg) in 1 ml of glacial acetic acid. After 30 minutes at room temperature, the solvent is removed by evaporation in vacuo. Traces of acetic acid is removed by several co-evaporation with toluene. The residue is dissolved in saturated methanolic ammonia (50 ml) and the mixture is kept standing at room temperature for 2 days. The solvent is removed by evaporation in vacuo and the residue is crystallized from water to give 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-bromouracil (325 mg), m.p. 214°-216°.

후처리

  1. customthe solvent is removed by evaporation in vacuo
  2. customTraces of acetic acid is removed by several co-evaporation with toluene
  3. dissolutionThe residue is dissolved in saturated methanolic ammonia (50 ml)
  4. waitthe mixture is kept standing at room temperature for 2 days
  5. customThe solvent is removed by evaporation in vacuo
  6. customthe residue is crystallized from water

출처 및 근거

ORD 기록
ord-700abcba259b44b2a186b06bf9a5a35f
출처 데이터셋
uspto-grants-1980_07
특허 번호
US04211773

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