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

HRID 1814357ノート

反応式

HRID 1814357 の反応式
[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

参加物

5

反応物 3

HCID 1049Pyridine2 回HCID 865882243-Benzyloxy-4-chlorosulfonyl-benzoic acid methyl esterHCID 86588238(S)-3-amino-4,4-diethoxy-butyric acid tert-butyl ester

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-70e1ba7854fd488b89ea8d30c71d2ce3
出典データセット
uspto-grants-2005_04
特許番号
US06875765B2

反応ノート

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