Triethylamine → HCID 67153255, 화합물

HRID 1879474노트

반응식

HRID 1879474 반응식
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]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 86653800HCID 86653800, 화합물2회HCID 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

생성물 1

HCID 67153255HCID 67153255, 화합물수율 89.6%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a36013c528ea45aa96571fe4c13b7c76
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314250B2

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