Sodium Iodide → tert-butyl 3-((8-(3-(3-(heptanoyloxymethyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

HRID 1751011노트

반응식

HRID 1751011 반응식
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][N:3]1[CH2:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].[C:32]([O:40][CH2:41][N:42]1[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=2[N:44]([CH2:51][CH2:52][CH2:53]Cl)[C:43]1=[O:55])(=[O:39])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC.CO.ClCCl>[C:32]([O:40][CH2:41][N:42]1[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=2[N:44]([CH2:51][CH2:52][CH2:53][N:9]2[CH2:10][CH2:11][C:6]3([N:5]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:4][N:3]([CH2:18][C:19]4[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=4)[C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C:2]3=[O:1])[CH2:7][CH2:8]2)[C:43]1=[O:55])(=[O:39])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 58046667Tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoateHCID 58046749(3-(3-chloropropyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)methyl heptanoate

생성물 1

HCID 58046664tert-butyl 3-((8-(3-(3-(heptanoyloxymethyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate수율 86%

시약·촉매·용매 2

HCID 6569Methyl Ethyl Ketone용매HCID 21226129Dichloromethane methanol용매

실험 절차

tert-Butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.200 g, 0.474 mmol), (3-(3-chloropropyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)methyl heptanoate (0.17 g, 0.474 mmol), sodium iodide (0.021 g, 0.142 mmol), and potassium carbonate (0.0983 g, 0.711 mmol) in 2-butanone (5 mL) were heated at 78° C. for 4 hours. The reaction was diluted with 10% methanol/dichloromethane, filtered, and evaporated. The residue was purified by PTLC (50% ethyl acetate/hexanes) to give product as foam (0.30 g, 86%); NMR (DMSO-d6); δ0.78 (t, J=6.4 Hz, 3H); 1.16 (m, 6H); 1.44-1.48 (m, 2H); 1.51 (s, 9H); 1.60 (m, 2H); 1.84-1.87 (m, 2H); 2.28 (t, J=6.8 Hz, 2H); 2.35 (m, 2H); 2.51-2.59 (m, 2H); 2.65-2.71 (m, 4H); 3.93 (t, J=6.8 Hz, 2H); 4.58 (s, 2H); 4.61 (s, 2H); 5.88 (s, 2H); 6.77 (t, J=7.2 Hz, 1H); 6.85 (d, J=8 Hz, 2H); 7.06-7.10 (m, 2H); 7.22 (t, J=8.4 Hz, 2H); 7.26-7.32 (m, 2H); 7.48-7.54 (m, 2H); 7.79 (s, 1H); 7.82-7.84 (m, 1H); MS for C43H55N5O6 m/z 738 (M+H)+.

후처리

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was purified by PTLC (50% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-9b6261e45ef1433ab0cf6b01a1c55a86
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156840B2

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