Triethylamine → ((3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(N-methylcyclopropanesulfonamido)butan-2-yl)-2-oxopiperidin-3-yl)methyl methanesulfonate

HRID 932273노트

반응식

HRID 932273 반응식
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([C@@:9]1([CH2:42][OH:43])[CH2:14][C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[C@@H:12]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[N:11]([C@@H:29]([CH2:39][CH3:40])[CH2:30][N:31]([CH3:38])[S:32]([CH:35]2[CH2:37][CH2:36]2)(=[O:34])=[O:33])[C:10]1=[O:41])[CH:7]=[CH2:8].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:43][CH2:42][C@:9]1([CH2:6][CH:7]=[CH2:8])[CH2:14][C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[C@@H:12]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[N:11]([C@@H:29]([CH2:39][CH3:40])[CH2:30][N:31]([CH3:38])[S:32]([CH:35]2[CH2:37][CH2:36]2)(=[O:33])=[O:34])[C:10]1=[O:41])(=[O:4])=[O:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68000440N-((S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-(hydroxymethyl)-2-oxopiperidin-1-yl)butyl)-N-methylcyclopropanesulfonamide

생성물 1

HCID 58573447((3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(N-methylcyclopropanesulfonamido)butan-2-yl)-2-oxopiperidin-3-yl)methyl methanesulfonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Methanesulfonyl chloride (0.200 ml, 2.59 mmol) was added to a solution of N-((S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-(hydroxymethyl)-2-oxopiperidin-1-yl)butyl)-N-methylcyclopropanesulfonamide (1.0 g, 1.725 mmol) and triethylamine (0.480 ml, 3.45 mmol) in DCM. The reaction was stirred for 2 hours. The reaction mixture was diluted with DCM and washed with HCl (1N) and satd NaCl and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as an oil. The product was purified by chromatography through a RediSep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.) (12 g), eluting with a gradient of 0% to 80% EtOAc in hexane, to provide the title compound as an oil. Mass Spectrum (ESI) m/z=657.2 (M+1).

후처리

  1. washwashed with HCl (1N) and satd NaCl
  2. dry with materialdried over Na2SO4
  3. filtrationThe solution was filtered
  4. concentrationconcentrated in vacuo
  5. customto give the crude material as an oil
  6. customThe product was purified by chromatography through a RediSep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.) (12 g)
  7. washeluting with a gradient of 0% to 80% EtOAc in hexane

출처 및 근거

ORD 기록
ord-ecc031e1915541a7bb6301a3e8995579
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296736B2

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