Triethylamine → 3-(benzyloxy)-N-cyclobutyl-6-methyl-4-oxo-4H-pyran-2-carboxamide

HRID 420475ノート

反応式

HRID 420475 の反応式
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[O:11][C:10]=1[C:17]([OH:19])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH:33]1([NH2:37])[CH2:36][CH2:35][CH2:34]1.CCN(CC)CC>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[O:11][C:10]=1[C:17]([NH:37][CH:33]1[CH2:36][CH2:35][CH2:34]1)=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 98564973-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acidHCID 12618374Cyclobutanamine, hydrochloride (1:1)

生成物 1

HCID 866117983-(benzyloxy)-N-cyclobutyl-6-methyl-4-oxo-4H-pyran-2-carboxamide収率 91.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of 3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid (2.5 g, 9.6 mmol, 1.0 equiv), 1,1′-carbonyldiimidazole (2.49 g, 15.37 mmol, 1.6 equiv) in DMF (20 mL) was stirred at 50° C. for 5 h. The mixture was cooled to room temperature. Cyclobutylamine hydrochloride (1.24 g, 11.52 mmol, 1.2 equiv) and Et3N (1.74 mL, 12.48 mmol, 1.3 equiv) was added, and the mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure. Purification by chromatography (1:1 hexanes/EtOAc, then EtOAc) provided the titled compound (2.76 g, 91.56%) as a yellow solid. M.p. 69.3-71.0° C.; 1H-NMR (CDCl3, 400 MHz) δ 1.51-1.72 (m, 4H, cyclobutyl H), 2.19-2.28 (m, 2H, cyclobutyl H), 2.37 (s, 3H, CH3), 4.39-4.41 (m, 1H, CH), 5.41 (s, 2H, OCH2Ph), 6.30 (s, 1H, CH), 7.39-7.49 (m, 5H, ArH), 7.86 (br, 1H, NH), and MS (m/z) 314 (M++1), 217, 91.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. stirringthe mixture was stirred overnight at room temperature
  3. customThe solvent was removed under reduced pressure
  4. customPurification by chromatography (1:1 hexanes/EtOAc

出典と根拠

ORDレコード
ord-8ae853224d534714891a808765ccfda6
出典データセット
uspto-grants-2012_01
特許番号
US08097624B2

反応ノート

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