Triethylamine → N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(1-ethyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanamide

HRID 909893노트

반응식

HRID 909893 반응식
C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.[CH3:19][O:20][CH:21]([O:30][CH3:31])[CH2:22][NH:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[CH2:32]([N:34]1[CH:38]=[C:37]([C:39]2[CH:40]=[C:41]([CH:50]=[CH:51][CH:52]=2)[CH2:42][CH2:43][O:44][CH2:45][CH2:46][C:47](O)=[O:48])[N:36]=[N:35]1)[CH3:33].C(N(CC)CC)C>C1COCC1.C(#N)C.C(OCC)(=O)C>[CH:24]1([N:23]([CH2:22][CH:21]([O:30][CH3:31])[O:20][CH3:19])[C:47](=[O:48])[CH2:46][CH2:45][O:44][CH2:43][CH2:42][C:41]2[CH:50]=[CH:51][CH:52]=[C:39]([C:37]3[N:36]=[N:35][N:34]([CH2:32][CH3:33])[CH:38]=3)[CH:40]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 3024915N-(2,2-dimethoxyethyl)cyclohexanamineHCID 670761313-(3-(1-Ethyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanoic acid

생성물 1

HCID 67075953N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(1-ethyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanamide

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
25 °C

실험 절차

A solution of T3P (1.41 mL) dissolved in THF (1.57M) was added in one portion to a stirred solution of N-(2,2-dimethoxyethyl)cyclohexanamine (0.24 mL), 3-(3-(1-ethyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanoic acid [Example 4, Step iv)] (0.45 g), and triethylamine (1.86 mL) in acetonitrile (5 mL) at 25° C. The resulting solution was stirred at 25° C. for 15 min. The reaction mixture was diluted with ethyl acetate (50 mL), and washed with saturated sodium hydrogen carbonate (20 mL). The organic layer was dried over magnesium sulfate, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0-70% ethyl acetate in isohexane to afford the subtitled compound (0.46 g). 1H NMR (400 MHz, CD3OD) δ 8.32 and 8.31 (2×s, 1H), 7.68 and 7.66 (2×s, 1H), 7.65-7.61 (m, 1H), 7.32 and 7.32 (2×t, J=7.5 Hz, 1H), 7.22-7.18 (m, 1H), 4.52 and 4.36 (2×t, J=5.3 Hz, 1H), 4.47 (q, J=7.3 Hz, 2H), 4.04-3.94 (m, 1H), 3.76-3.61 (m, 4H), 3.34 (s, 3H), 3.32 (s, 3H), 3.25 (d, J=5.1 Hz, 2H), 2.91-2.85 (m, 2H), 2.68-2.62 (m, 2H), 1.79-1.03 (m, 10H), 1.56 (t, J=7.4 Hz, 3H), a ˜1:1 mixture of rotamers is observed.

후처리

  1. washwashed with saturated sodium hydrogen carbonate (20 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product
  6. customThe crude product was purified by flash silica chromatography, elution gradient 0-70% ethyl acetate in isohexane

출처 및 근거

ORD 기록
ord-752f319f69cf41cea1a1243f19a3d437
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017602B2

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