Dichloromethane → 1-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid

HRID 254403노트

반응식

HRID 254403 반응식
F[C:2](F)(F)[C:3]([OH:5])=[O:4].O=S1(=O)C[CH2:12][CH:11](N)[CH2:10]1.CC[N:18]([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20].C(O[BH-](O[C:35](=[O:37])C)OC(=O)C)(=O)C.[Na+].Cl[CH2:40]Cl>O>[CH:22]([N:18]1[C:19]2[C:20](=[CH:10][CH:11]=[CH:12][CH:21]=2)[CH:40]=[C:2]([C:3]([OH:5])=[O:4])[C:35]1=[O:37])([CH3:23])[CH3:24]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 668595081,1-Dioxotetrahydro-1lambda6-thiophen-3-ylamine trifluoroacetic acid salt

생성물 1

HCID 109442901-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

1,1-dioxotetrahydro-1λ6-thiophen-3-ylamine trifluoroacetic acid salt (500 mg; 2 mmol), N,N′-diisopropylethylamine (0.35 mL), and sodium triacetoxyborohydride (422 mg; 2 mmol) was added to a vial containing 10 mL of dichloromethane. The mixture was stirred for 5 minutes prior to the addition of 1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid {(1S,3R,5R)-8-[(2,2-dihydroxy)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}amide (0.427 g). The final mixture was stirred for 1 h, at which time the reaction was judged to be complete based on HPLC and mass spectrometric analysis. Water (20 mL) was slowly added to quench the remaining reducing agent. The mixture was diluted with 100 mL of dichloromethane, and shaken in a funnel before collecting the organic layer. The organic layer was washed with 1M NaOH (40 mL) and brine (50 mL), dried over MgSO4, and evaporated to yield the title intermediate as a colorless solid. This crude product was used in the next step without further treatment.

후처리

  1. customto quench the
  2. additionThe mixture was diluted with 100 mL of dichloromethane
  3. stirringshaken in a funnel
  4. custombefore collecting the organic layer
  5. washThe organic layer was washed with 1M NaOH (40 mL) and brine (50 mL)
  6. dry with materialdried over MgSO4
  7. customevaporated

출처 및 근거

ORD 기록
ord-9c394f68528c481bb5cc3e879d0473c2
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875629B2

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