Potassium Carbonate → (1R,2R)-2-Amino-1-(4-azido-phenyl)-3-fluoro-propan-1-ol

HRID 1520509노트

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HRID 1520509 반응식
[NH2:1][C@@H:2]([CH2:12][F:13])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1)[OH:4].[N-:14]=[N+:15]=[N-:16].[Na+].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O.O>[NH2:1][C@@H:2]([CH2:12][F:13])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([N:14]=[N+:15]=[N-:16])=[CH:7][CH:6]=1)[OH:4]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 145742L-ProlineHCID 86695458(1R,2R)-2-Amino-3-fluoro-1-(4-iodo-phenyl)-propan-1-ol

생성물 1

HCID 86695457(1R,2R)-2-Amino-1-(4-azido-phenyl)-3-fluoro-propan-1-ol수율 84.4%

시약·촉매·용매 2

HCID 962Water용매HCID 23503278(Methanesulfinyl)methane--water (1/1)용매

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온도
60 °C

실험 절차

To the stirred solution of (1R,2R)-2-Amino-3-fluoro-1-(4-iodo-phenyl)-propan-1-ol (1 g, 3.38 mmol) in dimethylsulfoxide:water (9:1, 10 mL) is added NaN3 (0.26 g, 3.99 mmol), Na-ascorbate (0.1 g, 0.50 mmol), CuSO4.5H2O (0.17 g, 0.68 mmol), L-proline (78 mg, 0.67 mmol), K2CO3 (93 mg 0.67 mmol) and resulting reaction mixture heated to 60° C. for 5 hours. Diluted with cold water and extracted with ethylacetate and washed with excess of water and brine. Organic layer dried over sodium sulphate and solvent is evaporated in vacuo to get the crude title compound (0.6 g, crude), used as such in next step. LC-MS (m/z): [M+H]=211.2.

후처리

  1. customresulting
  2. customreaction mixture
  3. extractionextracted with ethylacetate
  4. washwashed with excess of water and brine
  5. dry with materialOrganic layer dried over sodium sulphate and solvent
  6. customis evaporated in vacuo

출처 및 근거

ORD 기록
ord-bba0fe90f26e47a890ef0a606617f0c2
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073894B2

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