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

HRID 1814371노트

반응식

HRID 1814371 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a28b643372c44d9d973b7da33e48efa8
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875765B2

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