Cesium carbonate → HCID 57968585、化合物

HRID 882758ノート

反応式

HRID 882758 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:22][CH2:21][CH2:20][N:19]([CH:23]2[CH2:26][CH2:25][CH2:24]2)[CH2:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CC1C=NC2C(C=1C)=CC=C1C=2N=CC(C)=C1C.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:22][CH2:21][CH2:20][N:19]([CH:23]2[CH2:24][CH2:25][CH2:26]2)[CH2:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 44600522HCID 44600522、化合物

生成物 1

HCID 57968585HCID 57968585、化合物収率 70%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a stirred suspension of (2S,4R)-2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (116 mg, 0.32 mmol) in toluene (0.65 ml) was added iodobenzene (129 mg, 0.63 mmol), copper (I) iodide (6 mg, 0.032 mmol), 3,4,7,8-tetramethyl-1,10-phenanthroline (15 mg, 0.063 mmol), and Cs2CO3 (206 mg, 0.63 mmol). The resulting suspension was heated at 100° C. in a capped scintillation vial with stirring for 2 days. The reaction mixture was filtered through diatomaceous earth, washing with CH2Cl2. The filtrate was dried and concentrated. Purification of the residue by FCC provided the desired product (97.7 mg, 70%). MS (ESI): mass calcd. for C25H37N3O4, 443.3; m/z found, 444.3 [M+H]+. 1H NMR (CDCl3): 7.30-7.25 (m, 2H), 6.96 (dd, J=14.5, 7.2 Hz, 1H), 6.85 (dd, J=7.7, 5.5 Hz, 1H), 5.04-4.91 (m, 1H), 4.88-4.71 (m, 1H), 3.89-3.43 (m, 6H), 2.92-2.79 (m, 1H), 2.70-2.20 (m, 6H), 2.07-1.74 (m, 7H), 1.71-1.52 (m, 2H), 1.43-1.41 (m, 9H).

後処理

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washwashing with CH2Cl2
  3. customThe filtrate was dried
  4. concentrationconcentrated
  5. customPurification of the residue by FCC

出典と根拠

ORDレコード
ord-eefb40f298aa4e079c590b6fb5d015d9
出典データセット
uspto-grants-2012_08
特許番号
US08236792B2

反応ノート

読み込み中…