Triphenylphosphine → Methyl 2-[3-(2-(carbazol-9-yl)ethoxy)phenylthio]isobutyrate

HRID 2223313

반응식

HRID 2223313 반응식
[OH:1][C:2]1[CH:3]=[C:4]([S:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH:16]1[C:28]2[N:27]([CH2:29][CH2:30]O)[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH:25]1[C:26]2[N:27]([CH2:29][CH2:30][O:1][C:2]3[CH:3]=[C:4]([S:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=3)[C:28]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]=2[CH:22]=[CH:23][CH:24]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 228287Carbazole-9-ethanolHCID 5363146Diisopropyl azodicarboxylateHCID 68621947Methyl 2-(3-hydroxyphenylthio)isobutyrate

생성물 1

HCID 10025091Methyl 2-[3-(2-(carbazol-9-yl)ethoxy)phenylthio]isobutyrate수율 45%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The title product was prepared according to the procedure described in Method B starting from methyl 2-(3-hydroxyphenylthio)iso-butyrate (prepared as described in example 1) (0.609 g, 2.7 mmol), 9H-carbazol-9-ethanol (0.570 g, 2.7 mmol), DIAD (0.708 g, 3.5 mmol), and triphenylphosphine (0.917 g, 3.5 mmol) added piecemeal in small portions, keeping the temperature below 30° C., in 14 mL of anhydrous THF. The reaction was left under magnetic stirring for 18 hours at room temperature. After this period, the solvent was evaporated and the residue purified by silica gel chromatography using hexane/AcOEt 9/1 as eluent. 0.510 g of product were obtained (yield: 45%); Mp: 101-103° C.; TLC: silica gel, eluent hexane/AcOEt 8/2, Fr: 0.38; 1H NMR (CDCl3, 300 MHz) δ: 8.05 (d, 2H), 7.50 (m, 4H), 7.15 (m, 2H), 7.08 (t, 1H), 7.00 (d, 1H), 6.90 (s, 1H), 6.80 (m, 1H), 4.75 (t, 2H), 4.35 (t, 2H), 3.60 (s, 3H), 1.40 (s, 6H); HPLC: Column: Symmetry—C18, (5 μm) 4.6×150 mm, T: room temperature, mobile phase CH3CN/H2O 65/35 (v/v), pH: as is, flow rate: 0.80 mL/min, 205 nm UV detector, retention time 11.45 min; E.A. conforming for C25H25NO3S.

후처리

  1. additionadded piecemeal in small portions
  2. customthe temperature below 30° C.
  3. waitThe reaction was left
  4. waitAfter this period
  5. customthe solvent was evaporated
  6. customthe residue purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-0fa7c68a04c649569bc661463ffa647d
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07375124B2

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