Triphenylphosphine → 4-((R)-1-Benzyloxycarbonyl-ethoxy)-7-methyl-quinoline-2-carboxylic acid methyl ester

HRID 1185558노트

반응식

HRID 1185558 반응식
Cl.[CH3:2][O:3][C:4]([C:6]1[CH:15]=[C:14]([OH:16])[C:13]2[C:8](=[CH:9][C:10]([CH3:17])=[CH:11][CH:12]=2)[N:7]=1)=[O:5].[CH2:18]([O:25][C:26](=[O:30])[C@H:27]([CH3:29])O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[CH3:2][O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][C@@H:27]([C:26]([O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:30])[CH3:29])[C:13]2[C:8](=[CH:9][C:10]([CH3:17])=[CH:11][CH:12]=2)[N:7]=1)=[O:5]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11052238benzyl (2S)-2-hydroxypropanoateHCID 178498501HCID 178498501, 화합물

생성물 1

HCID 685993014-((R)-1-Benzyloxycarbonyl-ethoxy)-7-methyl-quinoline-2-carboxylic acid methyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1.00 g 4-Hydroxy-7-methyl-quinoline-2-carboxylic acid methyl ester hydrochloride and 0.83 g benzyl-L-lactate in 30 ml THF were added 1.81 g triphenylphosphine and 1.20 g diethylazodicarboxylate. After 2 h LCMS indicated complete conversion and water was added to the reaction mixture which was subsequently extracted with ethyl acetate. The residue obtained after evaporation of the solvent was purified by flash chromatography on silica using an ethyl acetate/heptane gradient. Yield: 1.80 g.

후처리

  1. extractionwas subsequently extracted with ethyl acetate
  2. customThe residue obtained
  3. customafter evaporation of the solvent
  4. customwas purified by flash chromatography on silica using an ethyl acetate/heptane gradient

출처 및 근거

ORD 기록
ord-c70cc9f1ae454041ba3df0e844b7755f
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669266B2

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