Sodium Carbonate → tert-Butyl 3-((3-(1-(4-hydroxybutanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyloxy)carbonylamino)propanoate

HRID 2175284노트

반응식

HRID 2175284 반응식
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][N:7]2[C:12](=[O:17])[CH2:13][CH2:14][CH2:15][OH:16].CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.C([O-])(=O)C.[K+].Br[C:42]1[CH:43]=[C:44]([CH:59]=[CH:60][CH:61]=1)[CH2:45][O:46][C:47]([NH:49][CH2:50][CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])=[O:48].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.C(OCC)(=O)C.CO>[OH:16][CH2:15][CH2:14][CH2:13][C:12]([N:7]1[C:8]2[C:3](=[C:2]([C:42]3[CH:43]=[C:44]([CH:59]=[CH:60][CH:61]=3)[CH2:45][O:46][C:47]([NH:49][CH2:50][CH2:51][C:52]([O:54][C:55]([CH3:57])([CH3:58])[CH3:56])=[O:53])=[O:48])[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:5][CH2:6]1)=[O:17]

참가 물질

10

반응물 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 709827651-(5-Bromo-3,4-dihydroquinolin-1(2H)-yl)-4-hydroxybutan-1-oneHCID 70982800tert-Butyl 3-((3-bromobenzyloxy)carbonylamino)propanoate

생성물 1

HCID 70982571tert-Butyl 3-((3-(1-(4-hydroxybutanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyloxy)carbonylamino)propanoate수율 69.2%

시약·촉매·용매 4

HCID 178418807HCID 178418807, 화합물촉매2회HCID 887Methanol용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

To a degassed mixture of 1-(5-bromo-3,4-dihydroquinolin-1(2H)-yl)-4-hydroxybutan-1-one (0.208 g, 0.698 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (0.532 g, 2.094 mmol), and potassium acetate (0.411 g, 4.19 mmol) in DMF (10 mL) was added PdCl2(dppf)-CH2Cl2 (0.057 g, 0.070 mmol). The vial was purged with argon, sealed, and stirred at 90° C. for 2 d. tert-Butyl 3-((3-bromobenzyloxy)carbonylamino)propanoate (0.5 g, 1.396 mmol), PdCl2(dppf)-CH2Cl2 (0.057 g, 0.070 mmol), and 2 M Na2CO3 (2 mL, 1.396 mmol) were added. The reaction mixture was purged with argon and stirred at 95° C. overnight. At the conclusion of this period, the reaction mixture was quenched with water and extracted with ethyl acetate. The organic extract was dried, concentrated, and purified by flash chromatography (0-100% ethyl acetate:hexanes then 10% CH3OH:ethyl acetate) to afford the title compound (0.24 g, 69% yield) as a dark brown oil. LCMS, [M+H]+=497.4.

후처리

  1. customThe vial was purged with argon
  2. customsealed
  3. customThe reaction mixture was purged with argon
  4. stirringstirred at 95° C. overnight
  5. customAt the conclusion of this period, the reaction mixture was quenched with water
  6. extractionextracted with ethyl acetate
  7. extractionThe organic extract
  8. customwas dried
  9. concentrationconcentrated
  10. custompurified by flash chromatography (0-100% ethyl acetate

출처 및 근거

ORD 기록
ord-1ecb485f1753467490a67e676da99f76
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062028B2

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