Diethyl Ether → Methyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)-3-methyl-2-oxopiperidin-3-yl)acetate

HRID 932134노트

반응식

HRID 932134 반응식
[Si]([O:18][CH2:19][C@@H:20]([N:23]1[C@H:28]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[C@@H:27]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=2)[CH2:26][C@@:25]([CH2:44][C:45]([OH:47])=[O:46])([CH3:43])[C:24]1=[O:48])[CH2:21][CH3:22])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:49][Si](C=[N+]=[N-])(C)C.C(OCC)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CO.C1C=CC=CC=1.C1COCC1>[Cl:42][C:38]1[CH:37]=[C:36]([C@@H:27]2[C@@H:28]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[N:23]([C@@H:20]([CH2:21][CH3:22])[CH2:19][OH:18])[C:24](=[O:48])[C@:25]([CH2:44][C:45]([O:47][CH3:49])=[O:46])([CH3:43])[CH2:26]2)[CH:41]=[CH:40][CH:39]=1

참가 물질

8

반응물 4

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 2724141Tetrabutylammonium FluorideHCID 601541832-((3R,5R,6S)-1-((S)-1-(tert-butyldiphenylsilyloxy)butan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)acetic acid

생성물 1

HCID 58573771Methyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)-3-methyl-2-oxopiperidin-3-yl)acetate

시약·촉매·용매 3

HCID 241Benzene용매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2-((3R,5R,6S)-1-((S)-1-(tert-butyldiphenylsilyloxy)butan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)acetic acid (Example 185) in MeOH (2 mL) and benzene (8 mL) was stirred with (trimethylsilyl)diazomethane, 2.0 M in diethyl ether (2.02 mL, 4.04 mmol) at rt for 0.5 h. After that time the mixture was concentrated to give the crude methyl ester, which was treated with TBAF in THF at rt for 30 h. The mixture was concentrated and purified by chromatography on silica gel (0 to 100% EtOAc in hexanes) to give the title compound. Mass Spectrum (ESI) m/z=478 (M+1).

후처리

  1. concentrationAfter that time the mixture was concentrated
  2. customto give the crude methyl ester, which
  3. concentrationThe mixture was concentrated
  4. custompurified by chromatography on silica gel (0 to 100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-24902080712845f49ce56b642dca510a
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296736B2

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