Pyridine → (s)-3-(2-Benzyloxybenzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester

HRID 1814371ノート

反応式

HRID 1814371 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15](Cl)(=[O:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:23][C:24](=[O:35])[CH2:25][C@H:26]([NH2:34])[CH:27]([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])([CH3:22])([CH3:21])[CH3:20].N1C=CC=CC=1>C(Cl)(Cl)Cl.C(OCC)(=O)C>[C:19]([O:23][C:24](=[O:35])[CH2:25][C@H:26]([NH:34][S:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:17])=[O:16])[CH:27]([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])([CH3:21])([CH3:20])[CH3:22]

参加物

6

反応物 3

HCID 1049PyridineHCID 219624592-(Benzyloxy)benzene-1-sulfonyl chlorideHCID 86588238(S)-3-amino-4,4-diethoxy-butyric acid tert-butyl ester

生成物 1

HCID 69692460(s)-3-(2-Benzyloxybenzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester収率 91.2%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-Benzyloxy-benzenesulfonyl chloride (see Example 23, step 1) (1.7 g, 6 mmol) and (S)-3-amino-4,4-diethoxy-butyric acid tert-butyl ester (see Example 93) (1.5 g, 6 mmol) and pyridine (1.9 g, 30 mmol) were dissolved in chloroform (150 mL) and stirred at room temperature for 3 days. The reaction was diluted with ethyl acetate (500 mL) and washed with 5% citric acid, sat. sodium bicarbonate, and sat. sodium chloride. The organic layer was then dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash chromatography (SiO2, hexane:ethyl acetate, 8:1, then 4:1) gave the desired product (2.7 g, 91%) as a colorless oil. 1H NMR (400 MHz) CDCl3 δ 7.92 (m, 1H), 7.52 (d, 2H), 7.47 (t, 1H), 7.40 (t, 2H), 7.34 (d, 1H), 7.04 (t, 2H), 5.61 (d, 1H), 5.23 (q, 2H), 4.30 (d, 1H), 3.77 (m, 1H), 3.47 (m, 2H), 3.36 (m, 1H), 3.15 (m, 1H), 2.45 (t, 2H), 1.37 (s, 9H), 1.02 (t, 3H), 0.92 (t, 3H).

後処理

  1. washwashed with 5% citric acid, sat. sodium bicarbonate, and sat. sodium chloride
  2. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography (SiO2, hexane

出典と根拠

ORDレコード
ord-a28b643372c44d9d973b7da33e48efa8
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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