Sodium Thiosulfate → HCID 54538205, 화합물

HRID 429479노트

반응식

HRID 429479 반응식
[CH3:1][N:2]([CH2:18][C@H:19]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[CH2:20][CH:21]=C)[C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[N:13][N:12]=[N:11]2)[CH:7]=[CH:6][C:5]=1[O:15][CH3:16].C[N+]1([O-])CC[O:34]CC1.S([O-])([O-])(=O)=S.[Na+].[Na+].I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O.C(OCC)(=O)C.O.O1CCCC1.CC(C)=O.C(O)(C)(C)C.O>[CH3:1][N:2]([CH2:18][C@H:19]([C:23]1[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=1)[CH2:20][CH:21]=[O:34])[C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[N:13][N:12]=[N:11]2)[CH:7]=[CH:6][C:5]=1[O:15][CH3:16]

참가 물질

10

반응물 4

HCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 53841613HCID 53841613, 화합물

생성물 1

HCID 54538205HCID 54538205, 화합물

시약·촉매·용매 5

HCID 30318Osmium Tetroxide촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 86602953Acetone tBuOH Water용매

실험 절차

Combine (S)-N-methyl-N-(2-(4-fluorophenyl)pent-4-enyl)-2-methoxy-5-(1H-tetrazol-1-yl)benzamide (4.46 g, 11.3 mmol), acetone/t-butanol/water (2/1/1, 64 mL), and a solution of N-methylmorpholine N-oxide (3.0 mL, 50% in water, 14.5 mmol). Add a solution of osmium tetraoxide (3.0 mL, 4% in water, 0.5 mmol). After 3 hours, evaporate in vacuo to remove most of the acetone and partition the evaporated reaction mixture between dichloromethane and an aqueous 10% solution of sodium thiosulfate. Separate the layer, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Combine the residue, tetrahydrofuran (80 mL), and water (20 mL). Add sodium meta-periodate (3.63 g). After 1.5 hours, filter the reaction mixture, rinse the solids with dichloromethane, and evaporate the filtrate to obtain a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give the title compound: Rf=0.22 (silica gel, ethyl acetate).

후처리

  1. customevaporate in vacuo
  2. customto remove most of the acetone
  3. custompartition
  4. customthe evaporated reaction mixture between dichloromethane
  5. customSeparate the layer
  6. dry with materialdry the organic layer over MgSO4
  7. filtrationfilter
  8. customevaporate in vacuo
  9. customto give a residue
  10. waitAfter 1.5 hours
  11. filtrationfilter the reaction mixture
  12. washrinse the solids with dichloromethane
  13. customevaporate the filtrate
  14. customto obtain a residue

출처 및 근거

ORD 기록
ord-a4b0d0db0a044e82874b5610023af22e
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316445B1

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