Pyridine → 3-Benzyloxy-4-(1-tert-butoxycarbonylmethyl-2,2-diethoxy-ethylsulfamoyl)-benzoic acid methyl ester

HRID 1814357노트

반응식

HRID 1814357 반응식
[C:1]([O:5][C:6](=[O:17])[CH2:7][C@H:8]([NH2:16])[CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[CH3:24][O:25][C:26](=[O:45])[C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[C:29]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:28]=1>C(Cl)Cl>[CH3:24][O:25][C:26](=[O:45])[C:27]1[CH:32]=[CH:31][C:30]([S:33](=[O:35])(=[O:34])[NH:16][CH:8]([CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:17])[CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])=[C:29]([O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:28]=1

참가 물질

5

반응물 3

HCID 1049Pyridine2회HCID 865882243-Benzyloxy-4-chlorosulfonyl-benzoic acid methyl esterHCID 86588238(S)-3-amino-4,4-diethoxy-butyric acid tert-butyl ester

생성물 1

HCID 697315433-Benzyloxy-4-(1-tert-butoxycarbonylmethyl-2,2-diethoxy-ethylsulfamoyl)-benzoic acid methyl ester수율 90.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (S)-3-amino-4,4-diethoxy-butyric acid tert-butyl ester (3.38 g, 13.7 mmol) in anhydrous methylene chloride (130 mL) was added pyridine (3.3 mL, 41 mmol) followed by 3-benzyloxy-4-chlorosulfonyl-benzoic acid methyl ester (4.66 g, 13.7 mmol). The reaction was allowed to stir at room temperature overnight. Mass spectrometry and TLC analysis showed presence of starting material. An additional 2 equivalents of pyridine (2.2 mL, 27.3 mmol) was added and allowed to stir overnight. TLC analysis showed the reaction to be completed. The methylene chloride was evaporated and the reaction mixture was dissolved in ether and 5% aqueous citric acid. The organic layer was collected and washed with 5% citric acid and then brine, dried over magnesium sulfate, filtered, and concentrated to yield 3-benzyloxy-4-(1-tert-butoxycarbonylmethyl-2,2-diethoxy-ethylsulfamoyl)-benzoic acid methyl ester (6.82 g, 12.4 mmol, 90%) as an orange tar. MS (APCI) m/z 550.3 (M−1).

후처리

  1. stirringto stir overnight
  2. customthe reaction
  3. customThe methylene chloride was evaporated
  4. dissolutionthe reaction mixture was dissolved in ether
  5. customThe organic layer was collected
  6. washwashed with 5% citric acid
  7. dry with materialbrine, dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-70e1ba7854fd488b89ea8d30c71d2ce3
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875765B2

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