Phenyl chloroformate → Phenyl (4-{4-[(3S)-3-methylmorpholin-4-yl]-6-[(phenylsulfonyl)methyl]pyrimidin-2-yl}phenyl)carbamate

HRID 2353656노트

반응식

HRID 2353656 반응식
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[C:12]([CH2:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[N:11]=[C:10]([C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[N:9]=1.C(=O)(O)[O-].[Na+].Cl[C:37]([O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:38]>O1CCOCC1>[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[C:12]([CH2:14][S:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[N:11]=[C:10]([C:24]2[CH:25]=[CH:26][C:27]([NH:30][C:37](=[O:38])[O:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:28][CH:29]=2)[N:9]=1

참가 물질

5

반응물 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59380145(4-{4-[(3S)-3-Methylmorpholin-4-yl]-6-[(phenylsulfonyl)methyl]pyrimidin-2-yl}phenyl)amine

생성물 1

HCID 59380153Phenyl (4-{4-[(3S)-3-methylmorpholin-4-yl]-6-[(phenylsulfonyl)methyl]pyrimidin-2-yl}phenyl)carbamate수율 42.9%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

(4-{4-[(3S)-3-Methylmorpholin-4-yl]-6-[(phenylsulfonyl)methyl]pyrimidin-2-yl}phenyl)amine (2 g, 4.71 mmol) was dissolved in dioxane (20 mL). Sodium bicarbonate (594 mg, 7.07 mmol) was added, followed by phenyl chloroformate (0.593 mL, 4.71 mmol) and the reaction stirred at room temperature for 2 hours. The solvent was removed in vacuo, and the resultant oil partitioned between 20 mL DCM and 20 mL water. The organic phase was dried over magnesium sulphate, filtered and concentrated in vacuo. The cream solid obtained was chromatographed on silica, eluting with 0-50% ethyl acetate in DCM, to give the desired material as a white solid (1.1 g).

후처리

  1. customThe solvent was removed in vacuo
  2. customthe resultant oil partitioned between 20 mL DCM and 20 mL water
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe cream solid obtained
  7. customwas chromatographed on silica
  8. washeluting with 0-50% ethyl acetate in DCM

출처 및 근거

ORD 기록
ord-7658c7230b774345b186374c1a7ecf95
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07750003B2

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