Hydrochloric Acid → (Z)-(1S,4R,6S,18R)-18-[2-(4-ethynyl-thiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid

HRID 388655노트

반응식

HRID 388655 반응식
C[O:2][C:3]([C@@:5]12[CH2:23][C@H:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH3:24])[C:14](=[O:25])[N:13]1[C@@H:8]([CH2:9][C@H:10]([O:26][C:27]3[C:36]4[C:31](=[C:32]([CH3:39])[C:33]([O:37][CH3:38])=[CH:34][CH:35]=4)[N:30]=[C:29]([C:40]4[S:41][CH:42]=[C:43]([C:45]#[CH:46])[N:44]=4)[CH:28]=3)[CH2:11][CH2:12]1)[C:7](=[O:47])[NH:6]2)=[O:4].[Li+].[OH-].Cl>O1CCCC1.O>[C:45]([C:43]1[N:44]=[C:40]([C:29]2[CH:28]=[C:27]([O:26][C@H:10]3[CH2:9][C@@H:8]4[N:13]([C:14](=[O:25])[N:15]([CH3:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][C@H:22]5[C@:5]([C:3]([OH:4])=[O:2])([NH:6][C:7]4=[O:47])[CH2:23]5)[CH2:12][CH2:11]3)[C:36]3[C:31](=[C:32]([CH3:39])[C:33]([O:37][CH3:38])=[CH:34][CH:35]=3)[N:30]=2)[S:41][CH:42]=1)#[CH:46]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 87472167(Z)-(1S,4R,6S,18R)-18-[2-(4-ethynyl-thiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid methyl ester

생성물 1

HCID 87472044(Z)-(1S,4R,6S,18R)-18-[2-(4-ethynyl-thiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid수율 46%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of compound 37 (0.11 g, 1 eq.) and LiOH (0.022 g, 5 eq.) in a mixture of tetrahydrofuran (5 mL) and water (5 mL) was stirred at room temperature overnight. HCl (1N) was added and the mixture was extracted with dichloromethane. Dried organics were evaporated in vacuo. The crude residue was purified by chromatography on silica gel to give compound 38 in 46% yield. MS (ESI, EI+) m/z=644 (MH+).

후처리

  1. extractionthe mixture was extracted with dichloromethane
  2. customDried organics were evaporated in vacuo
  3. customThe crude residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-c7ba6fde23a54dad91b6694836b4561d
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377962B2

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