1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10239859, 화합물

HRID 458458

반응식

HRID 458458 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:18]([CH2:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[N:17][C:9]2[C@H:10]3[N:14]([C:15](=[O:16])[C:8]=2[C:7]=1[C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=1)[CH2:13][CH2:12][CH2:11]3)=[O:5])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:55][C@H:56]1[C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[CH2:58][CH2:57]1>ClCCl>[C@H:56]1([NH:55][C:29]([C:28]2[CH:27]=[CH:26][C:25]([C:7]3[C:8]4[C:15](=[O:16])[N:14]5[C@H:10]([C:9]=4[N:17]=[C:18]([CH2:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[C:6]=3[C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:12][CH2:13]5)=[CH:33][CH:32]=2)=[O:30])[C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[CH2:58][CH2:57]1

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2733933(R)-(-)-1-AminoindanHCID 69742476HCID 69742476, 화합물

생성물 1

HCID 10239859HCID 10239859, 화합물수율 20%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 4-[(9aS)-3-(ethoxycarbonyl)-2-(4-methylpentyl)-5-oxo-7,8,9,9a-tetrahydro-5H-pyrido[2,3-α]pyrrolizin-4-yl]benzoic acid (0.100 g, 0.222 mmol) in 1 mL of dichloromethane, EDCI (0.051 g, 0.266 mmol), HOBT (0.036 g, 0.266 mmol) and (R)-(−)-1-aminoindane (0.065 g, 0.444 mmol) were added. The reaction mixture was allowed to stir for ˜3 h. The reaction mixture was concentrated and redissolved in 1 mL of ethyl acetate. The organics were then washed with saturated aqueous NaHCO3 and brine. Filtration and concentration provided a brown oil which was purified by radial chromatography chromatography (ethyl acetate/hexanes (4:1)) to yield 0.013 g (20%) of the desired product as a tan solid: 1H NMR (CDCl3, 400 MHz) δ 7.83–7.76 (d, 2H, J=7.9), 7.44–7.38 (d, 2H, J=7.93), 7.35–7.29 (d, 1H, J=7.76), 7.27–7.17 (m, 3H), 6.52–6.44 (m, 1H), 5.71–5.63 (q, 1H, J=7.41), 4.70–4.63 (dd, 1H, J=10.3, J=6.38), 4.09–3.94 (m, 2H), 3.68–3.56 (m, 1H), 3.35–3.24 (m, 1H), 3.07–2.95 (m, 1H), 2.95–2.76 (m, 3H), 2.74–2.58 (m, 1H), 2.51–2.40 (m, 1H), 2.35–2.19(m, 2H), 1.97–1.84 (m, 1H), 1.83–1.64 (m, 2H), 1.61–1.48 (m, 1H), 1.43–1.31 (m, 1H), 1.30–1.20 (m, 2H), 1.01–0.93 (t, 3H, J=7.09), 0.89–0.81 (d, 6H, J=6.55); low resolution MS (ES+) m/e 566 (MH); RP-HPLC (BDS Hypersil C-18 25 cm×4.6 mm; 10–100% CH3CN in H2O with 0.1% TFA buffer; 30 minutes; 1 mL/min) tr=23.8 min, 99.9% purity.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionredissolved in 1 mL of ethyl acetate
  3. washThe organics were then washed with saturated aqueous NaHCO3 and brine
  4. filtrationFiltration and concentration
  5. customprovided a brown oil which
  6. customwas purified by radial chromatography chromatography (ethyl acetate/hexanes (4:1))

출처 및 근거

ORD 기록
ord-690299b4cb29442b89ffeb85bd8469a9
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189851B2

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