Phosphate → Methyl 2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole-7-carboxylate

HRID 1839308노트

반응식

HRID 1839308 반응식
[CH2:1]([Sn:5](Cl)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[S:15]1[CH:19]=[CH:18][N:17]2[CH:20]=[N:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:16]12.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CCCCCC.P([O-])([O-])([O-])=O>C1COCC1.ClCCl>[CH2:1]([Sn:5]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:6][CH2:7][CH2:8][CH3:9])[C:19]1[S:15][C:16]2=[C:22]([C:23]([O:25][CH3:26])=[O:24])[N:21]=[CH:20][N:17]2[CH:18]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

7

반응물 4

HCID 1061PhosphateHCID 15096Tributyltin ChlorideHCID 23448997Methyl imidazo[5,1-b]thiazole-7-carboxylateHCID 86588928Lithium bis(trimethylsilyl)amide hexane

생성물 1

HCID 23449182Methyl 2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole-7-carboxylate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-50 °C

실험 절차

A solution (5 ml) of 0.716 g of tri-n-butylstannyl Chloride in THF was added to a solution (20 ml) of 0.364 g of methyl imidazo[5,1-b]thiazole-7-carboxylate in THF at −70° C. A 1.0 N lithiumbis(trimethylsilyl)amide/n-hexane solution (4.4 ml) was added dropwise thereto at −70° C. The mixture was stirred at −50° C. for 30 min. The reaction solution was added to an ice cold mixed solution composed of 50 ml of 0.2 N phosphate buffer (ph 7) and 50 ml of dichloromethane with stirring. The organic layer was separated, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was subjected to separation and purification by flash column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 0.395 g of the title, compound.

후처리

  1. customat −70° C
  2. stirringwith stirring
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation
  6. customThe residue was subjected to separation and purification by flash column chromatography on silica gel (hexane:ethyl acetate=1:1)
  7. customto give 0.395 g of the title, compound

출처 및 근거

ORD 기록
ord-5baaa9b65e3c4322bf777745abb5ef58
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677331B2

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