(S)-3-(4-acetylamino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester → (S)-3-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester

HRID 1814367노트

반응식

HRID 1814367 반응식
[C:1]([O:5][C:6](=[O:38])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:29])[CH3:28])=[CH:22][C:21]=1[O:30]CC1C=CC=CC=1)(=[O:19])=[O:18])[CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].O1CCCC1>[C:1]([O:5][C:6](=[O:38])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:29])[CH3:28])=[CH:22][C:21]=1[OH:30])(=[O:19])=[O:18])[CH:9]([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15])([CH3:3])([CH3:4])[CH3:2]

참가 물질

5

반응물 2

HCID 69692085(S)-3-(4-acetylamino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl esterHCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 69692589(S)-3-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester수율 98.3%

시약·촉매·용매 2

HCID 23938Palladium촉매2회HCID 8028Tetrahydrofuran용매

실험 절차

11.4 g (20.7 mmol) (S)-3-(4-Acetylamino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester, 1 g 20% Pd/C, and 100 mL tetrahydrofuran was shaken under a 50 psi hydrogen atmosphere for 19 h. TLC analysis indicated incomplete reaction, so an additional 1 g 20% Pd/C was added and the reaction shaken an additional 20 h under a 50 psig hydrogen atmosphere. TLC showed complete reaction. The catalyst was filtered and the resulting solution was concentrated to give an oil. The product was purified over silica eluting with ethyl acetate to yield 9.37 g (20.34 mmol, 98.3%) of (S)-3-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester as an ivory-yellow solid. MS (APCI) m/z 459.1 (M−1).

후처리

  1. customreaction
  2. customreaction
  3. filtrationThe catalyst was filtered
  4. concentrationthe resulting solution was concentrated
  5. customto give an oil
  6. customThe product was purified over silica eluting with ethyl acetate

출처 및 근거

ORD 기록
ord-0ad54c53922441a49aa7bcdecc6e896e
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875765B2

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