Diisopropylcarbodiimide → HCID 178453874、化合物

HRID 1497028ノート

反応式

HRID 1497028 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[Cl:29])/[C:22](=[N:24]/O)/[NH2:23].CC(C)N=C=NC(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C.N1C=CC=CC=1.CCOC(C)=O>[Cl:18][C:19]1[CH:20]=[C:21]([C:22]2[N:24]=[C:15]([C@@H:12]3[CH2:11][CH2:10][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:14][CH2:13]3)[O:17][N:23]=2)[CH:26]=[CH:27][C:28]=1[Cl:29]

参加物

8

反応物 3

HCID 12734DiisopropylcarbodiimideHCID 112641853,4-Dichloro-N'-hydroxybenzene-1-carboximidamideHCID 178453971HCID 178453971、化合物

生成物 1

HCID 178453874HCID 178453874、化合物収率 57.9%

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A microwave vial was charged with cis-4-(tert-butoxycarbonylamino)cyclohexanecarboxylic acid (0.24 g, 0.98 mmol), DMAP (0.12 g, 0.98 mmol) and Intermediate 33A (0.20 g, 0.98 mmol). The reactants were dissolved in DMF (1 mL) and DIC (0.15 mL, 0.98 mmol) was added. The reaction mixture was stirred at rt for 14 h. The reaction mixture was diluted in 3 mL of pyridine. The vial was capped and the reaction mixture was heated in the microwave at 145° C. for 20 minutes, allowed to cool to rt, diluted with EtOAc and washed with water and brine. The solution were concentrated under reduced pressure and purified by flash chromatography with EtOAc/hexanes to give Intermediate 33B (233 mg, 0.565 mmol, 57.9% yield) as a white solid. LCMS=434.1 [M+1], RT=2.43 min (Method B); 1H NMR (500 MHz, chloroform-d) δ ppm 8.19 (1H, d, J=1.93 Hz), 7.92 (1H, dd, J=8.53, 1.93 Hz), 7.56 (1H, d, J=8.25 Hz), 4.59 (1H, br. s.), 3.71 (1H, d, J=9.63 Hz), 3.14-3.22 (1H, m), 2.07-2.17 (2H, m), 1.92-2.02 (2H, m), 1.84 (2H, td, J=8.67, 4.13 Hz), 1.62-1.73 (2H, m), 1.44 (9H, s).

後処理

  1. customThe vial was capped
  2. temperaturethe reaction mixture was heated in the microwave at 145° C. for 20 minutes
  3. temperatureto cool to rt
  4. washwashed with water and brine
  5. concentrationThe solution were concentrated under reduced pressure
  6. custompurified by flash chromatography with EtOAc/hexanes

出典と根拠

ORDレコード
ord-1e1a5803fc7a49bb97c0f57f7e6e582b
出典データセット
uspto-grants-2015_12
特許番号
US09199946B2

反応ノート

読み込み中…