Triethylamine → HCID 67153255、化合物

HRID 1879474ノート

反応式

HRID 1879474 の反応式
Cl.[CH3:2][C:3]([CH3:12])([CH3:11])[CH2:4][C@H:5]([NH2:10])[CH2:6][N:7]([CH3:9])[CH3:8].C(N(CC)CC)C.[CH3:20][C@@H:21]1[C@@H:26]([NH:27][C:28]([CH:30]2[CH2:34][CH2:33][S:32](=[O:36])(=[O:35])[N:31]2[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([CH:44]=O)[CH:39]=2)=[O:29])[CH2:25][C@H:24]2[CH2:46][C@@H:22]1[C:23]2([CH3:48])[CH3:47].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH3:20][C@@H:21]1[C@@H:26]([NH:27][C:28]([CH:30]2[CH2:34][CH2:33][S:32](=[O:36])(=[O:35])[N:31]2[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][NH:10][C@H:5]([CH2:6][N:7]([CH3:9])[CH3:8])[CH2:4][C:3]([CH3:12])([CH3:11])[CH3:2])[CH:39]=2)=[O:29])[CH2:25][C@H:24]2[CH2:46][C@@H:22]1[C:23]2([CH3:47])[CH3:48]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 86653800HCID 86653800、化合物2 回HCID 872885452-(3-formyl-benzyl)-1,1-dioxo-1lambda6-isothiazolidine-3-carboxylic acid((1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-amide

生成物 1

HCID 67153255HCID 67153255、化合物収率 89.6%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒2 回

実験手順

To a stirred solution of (S)-4,4,N1,N1-tetramethyl-pentane-1,2-diamine hydrochloride salt (Intermediate 2, 0.100 g, 0.43 mmol) in methanol (5 mL) at 0° C. was added triethylamine (0.12 g, 0.16 ml, 1.2 mmol). After 10 min of stirring at the same temperature, a solution of 2-(3-formyl-benzyl)-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid((1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-amide (0.181 g, 0.43 mmol) in methanol (1 mL) was added and stirring was continued for an additional 15 min at room temperature. The reaction mixture was again brought into 0° C. and sodium cyanoborohydride (0.022 g, 0.35 mmol) and acetic acid (0.2 mL) were added simultaneously into the reaction mixture. After stirring overnight at room temperature, the reaction mixture was concentrated under reduced pressure, the residue was diluted with ethyl acetate (5 mL), washed with water (3 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide crude 2-{3-[((S)-1-dimethylaminomethyl-3,3-dimethyl-butylamino)methyl]-benzyl}-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid((1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-amide (0.216 g, 89%).

後処理

  1. stirringstirring
  2. waitwas continued for an additional 15 min at room temperature
  3. customwas again brought into 0° C.
  4. stirringAfter stirring overnight at room temperature
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. additionthe residue was diluted with ethyl acetate (5 mL)
  7. washwashed with water (3 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a36013c528ea45aa96571fe4c13b7c76
出典データセット
uspto-grants-2012_11
特許番号
US08314250B2

反応ノート

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