Triethylamine → Ethyl 2-[[[(S)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazol-1-yl]carbonyl](methyl)amino]ethyl carbonate

HRID 2096082노트

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HRID 2096082 반응식
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[NH:7][C:8]([S@:10]([CH2:12][C:13]3[C:18]([CH3:19])=[C:17]([O:20][CH3:21])[C:16]([CH3:22])=[CH:15][N:14]=3)=[O:11])=[N:9][C:5]=2[CH:4]=1.[C:25](=[O:37])([O:34][CH2:35][CH3:36])[O:26][CH2:27][CH2:28][N:29]([C:31](Cl)=[O:32])[CH3:30].C(N(CC)CC)C.C(=O)(OCCN(C(N1C2C=C(OC)C=CC=2N=C1[S@](CC1C(C)=C(OC)C(C)=CN=1)=O)=O)C)OCC>O1CCCC1.CN(C)C1C=CN=CC=1>[C:25](=[O:37])([O:26][CH2:27][CH2:28][N:29]([C:31]([N:7]1[C:6]2[CH:23]=[CH:24][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[N:9]=[C:8]1[S@:10]([CH2:12][C:13]1[C:18]([CH3:19])=[C:17]([O:20][CH3:21])[C:16]([CH3:22])=[CH:15][N:14]=1)=[O:11])=[O:32])[CH3:30])[O:34][CH2:35][CH3:36]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 9568614EsomeprazoleHCID 116081722-[(Chlorocarbonyl)(methyl)amino]ethyl ethyl carbonateHCID 66894951ethyl 2-[[[(S)-6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazol-1-yl]carbonyl](methyl)amino]ethyl carbonate

생성물 1

HCID 10075300Ethyl 2-[[[(S)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazol-1-yl]carbonyl](methyl)amino]ethyl carbonate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a solution of (S)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole (1.34 g) synthesized by a method described in Synthetic Example 1 of JP-A 10-504290 in tetrahydrofuran (10 mL) were added 2-[(chlorocarbonyl)(methyl)amino]ethyl ethyl carbonate (0.9 mL) obtained in Reference Synthetic Example 34, triethylamine (1.08 mL) and 4-dimethylaminopyridine (0.010 g), and stirred at 60° C. for 6 hrs. The reaction solution was concentrated under reduced pressure, and to the residue was added water (30 mL), and extracted with ethyl acetate (50 mL). The ethyl acetate layer was washed with saturated brine (15 mL), and dried over anhydrous magnesium sulfate. After concentrating under reduced pressure, the residue was purified with basic silica gel column chromatography (eluted with ethyl acetate:hexane=1:2, then 1:1) to give a mixture of 3:2 of title compound and ethyl 2-[[[(S)-6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazol-1-yl]carbonyl](methyl)amino]ethyl carbonate as pale yellow amorphous solid (0.92 g).

후처리

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionto the residue was added water (30 mL)
  3. extractionextracted with ethyl acetate (50 mL)
  4. washThe ethyl acetate layer was washed with saturated brine (15 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationAfter concentrating under reduced pressure
  7. customthe residue was purified with basic silica gel column chromatography (
  8. washeluted with ethyl acetate
  9. customhexane=1:2, then 1:1) to give

출처 및 근거

ORD 기록
ord-b8a31f7bca5c4be5825e86ee1ece4dae
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08449911B2

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