Triethylamine → 2-fluorophenyl N-[7-(2-methyl-4,5-diphenyl-1H-imidazol-1-yl)heptan-2-yl]carbamate

HRID 1351019ノート

反応式

HRID 1351019 の反応式
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[CH3:18][CH:19]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[C:32]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:31]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:30]=[C:29]1[CH3:45])C(O)=O.C([N:48]([CH2:51]C)CC)C.[F:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=1[OH:60]>C1(C)C=CC=CC=1.O.ClCCl.C(OCC)(=O)C>[F:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=1[O:60][C:51](=[O:8])[NH:48][CH:19]([CH3:18])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[C:32]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[C:31]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:30]=[C:29]1[CH3:45]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 97072-FluorophenolHCID 199401P,P-Diphenylphosphinic azideHCID 185375322-Methyl-7-(2-methyl-4,5-diphenyl-imidazol-1-yl)-heptanoic acid

生成物 1

HCID 101170002-fluorophenyl N-[7-(2-methyl-4,5-diphenyl-1H-imidazol-1-yl)heptan-2-yl]carbamate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

(Scheme 3 (Q)) Diphenylphosphoryl Azide (0.083 ml, 0.38 mmole) was added to a suspension of starting material 2-methyl-7-(2-methyl-4,5-diphenyl-imidazol-1-yl)-heptanoic acid (120 mg, 0.32 mmole) and Triethylamine (0.14 ml, 1.005 mmole) in Toluene (5 ml) at room temperature. The reaction mixture was let stirred at room temperature for 10 minutes under Nitrogen, then at 108° C. for 90 minutes. The reaction was let cooled to room temperature, to which 2-Fluorophenol (0.03 ml, 0.038 g, 0.338 mmole) was added. The reaction mixture was let stirred at room temperature for 30 minutes, then at 100° C. for 18 hrs. The next day, analysis by TLC (Dichloromethane/Ethyl Acetate 3:1) indicated consumption of starting material. The reaction was let cooled to room temperature, where the solvent was removed by rotorvap. The crude material was purified by flash column chromatography using Dichloromethane/Ethyl Acetate (6:1 to 3:1). Product was obtained (110 mg, 71%). 1H NMR (CDCl3): δ1.21 (d, J=8.75 mHz, 6H), 1.35 (m, 2H), 1.51 (m, 2H), 2.50 (s, 3H), 3.71 (m, 3H), 4.93 (b, 1H), 7.18 (m, 6H), 7.32 (m, 2H), 7.46 (m, 6H). 13C NMR (CDCl3): 813.7, 21.1, 25.2, 30.3, 36.7, 43.7, 47.5, 116.5, 116.650, 124.132, 124.325, 125.943, 126.520, 128.027, 128.347, 128.509, 129.018, 131.101, 131.796, 134.8, 136.4, 138.6, 144.1, 153.0, 153.7, 155.6. Anal. Calcd. for C30H32FN3O20.42 H2O: C, 73.06; H, 6.71; N, 8.52. Found: C, 73.24; H, 6.82; N, 8.29. Mass Spec: 486.27 (MH+).

後処理

  1. waitat 108° C. for 90 minutes
  2. additionwas added
  3. stirringThe reaction mixture was let stirred at room temperature for 30 minutes
  4. waitat 100° C. for 18 hrs
  5. customconsumption of starting material
  6. temperatureThe reaction was let cooled to room temperature
  7. customwhere the solvent was removed by rotorvap
  8. customThe crude material was purified by flash column chromatography
  9. customProduct was obtained (110 mg, 71%)

出典と根拠

ORDレコード
ord-a363fe6e751e43dead4062a0d4f9a0c7
出典データセット
uspto-grants-2007_05
特許番号
USRE039634E1

反応ノート

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