Triethylamine → (2S,3R)-3-Ethylsulfanyl-2-(4'-fluoro-biphenyl-4-sulfonylamino)-3-phenyl-propionic Acid

HRID 2122023

반응식

HRID 2122023 반응식
C[O:2][C:3](=[O:32])[C@H:4]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C@H:5]([S:12][CH2:13][CH3:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.COC(=O)[C@H](N)[C@H](SCC)C1C=CC=CC=1.C(N(CC)CC)C.FC1C=CC(C2C=CC(S(Cl)(=O)=O)=CC=2)=CC=1>C(Cl)Cl>[CH2:13]([S:12][C@H:5]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C@@H:4]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C:3]([OH:32])=[O:2])[CH3:14]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 27947494'-Fluorobiphenyl-4-sulfonyl chlorideHCID 69881323(2S,3R)-3-Ethylsulfanyl-2-(4'-fluoro-biphenyl-4-sulfonylamino)-3-phenyl-propionic acid methyl esterHCID 69882615(2S,3R)-2-amino-3-ethylsulfanyl-3-phenyl-propionic acid methyl ester

생성물 1

HCID 9825456(2S,3R)-3-Ethylsulfanyl-2-(4'-fluoro-biphenyl-4-sulfonylamino)-3-phenyl-propionic Acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

(2S,3R)-3-Ethylsulfanyl-2-(4′-fluoro-biphenyl-4-sulfonylamino)-3-phenyl-propionic acid methyl ester. To a solution of (2S,3R)-2-amino-3-ethylsulfanyl-3-phenyl-propionic acid methyl ester 4a (49 mg, 0.20 mmol) in methylene chloride (2.0 mL) is added triethylamine (0.060 mL, 0.43 mmol) and 4′-fluoro-4-biphenylsulfonyl chloride (66 mg, 0.24 mmol). This mixture is stirred under argon overnight at room temperature. The reaction is diluted with methylene chloride and washed with 1.0 N aq. HCl. The aqueous layer is extracted with methylene chloride. The combined organic layers are dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified by column chromatography (silica gel, 20% EtOAc/hexanes) to give the desired product.

후처리

  1. washwashed with 1.0 N aq. HCl
  2. extractionThe aqueous layer is extracted with methylene chloride
  3. dry with materialThe combined organic layers are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by column chromatography (silica gel, 20% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-26b264d9ff03404fbef14fb6ef965191
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06696456B1

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