Sodium hydride → HCID 86619736, 화합물

HRID 1921204노트

반응식

HRID 1921204 반응식
[H-].[Na+].Br[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[S:12]1[CH2:17][CH2:16][CH:15]([N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[NH:20][C:19]2=[O:27])[CH2:14][CH2:13]1>CN(C=O)C>[O:27]=[C:19]1[N:20]([CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N:18]1[CH:15]1[CH2:16][CH2:17][S:12][CH2:13][CH2:14]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 67336664HCID 67336664, 화합물

생성물 1

HCID 86619736HCID 86619736, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium hydride (68.3 mg of a 60% dispersion in mineral oil, 1.71 mmol) followed by tert-butyl bromoacetate (0.189 mL, 1.28 mmol) was added to a solution of 1-tetrahydro-2H-thiopyran-4-yl-1,3-dihydro-2H-benzimidazol-2-one from Step B (200 mg, 0.854 mmol) in DMF (5 mL). After 1 h, the reaction was quenched with H2O (10 mL) and extracted with CH2Cl2 (10 mL). The organic layer was washed with saturated NaHCO3 (5 mL), dried over MgSO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 50:50, gave the title compound. MS: m/z=349 (M+1).

후처리

  1. customthe reaction was quenched with H2O (10 mL)
  2. extractionextracted with CH2Cl2 (10 mL)
  3. washThe organic layer was washed with saturated NaHCO3 (5 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography
  8. washeluting with a gradient of hexane

출처 및 근거

ORD 기록
ord-7bf23c4841044535be6b418bf792e291
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173655B2

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