Triethylamine → HCID 53973617, 화합물

HRID 849854노트

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HRID 849854 반응식
[CH3:1][NH:2][C@@H:3]([C:11]1[O:15][C:14]([C:16]([NH2:18])=[O:17])=[N:13][N:12]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(OC([CH2:26][NH:27][C@H:28]([CH2:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=1)[C:29]([OH:31])=O)=O)(C)(C)C.ON1C2N=C[CH:51]=[CH:52][C:47]=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH2:65](N(CC)CC)C.[C:72]([O:75]CC)(=[O:74])C>ClCCl.CN(C=O)C.O>[C:52]([O:75][C:72](=[O:74])[N:27]([C@@H:28]([C:29](=[O:31])[N:2]([C@@H:3]([C:11]1[O:15][C:14]([C:16](=[O:17])[NH2:18])=[N:13][N:12]=1)[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH3:1])[CH2:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=1)[CH3:26])([CH3:51])([CH3:47])[CH3:65]

참가 물질

10

반응물 6

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53913605HCID 53913605, 화합물HCID 54532855HCID 54532855, 화합물

생성물 1

HCID 53973617HCID 53973617, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

5-((1R)-1-Methylamino-2-phenylethyl)-[1,3,4]oxadiazole-2-carboxylic acid amide (240 mg, 0.98 mmol), (R)-2-((tert-butoxycarbonyl)methylamino)-3-(2-naphthyl)propionic acid (320 mg, 0.98 mmol) and 1-hydroxy-7-azabenzotriazole (133 mg, 0.98 mmol) were dissolved in dichloromethane (8 ml) and DMF (4 ml). The solution was cooled to 0° C. and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (230 mg, 1.18 mmol) was added. After 10 min triethylamine (0.35 ml, 2.46 mmol) was added. The solution was stirred for 1 h at 0° C. and subsequently for 16 h at room temp. The solution was diluted with ethyl acetate (30 ml) and water (20 ml). The phases were separated and the aqueous phase was extracted with ethyl acetate (20 ml). The combined organic layers were washed with a saturated solution of sodium hydrogencarbonate (30 ml) and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (50 g) with ethyl acetate to give 301 mg of ((1R)-1-(((1R)-1-(5-carbamoyl-[1,3,4]oxadiazol-2-yl)-2-phenylethyl)methylcarbamoyl)-2-(2-naphthyl)ethyl)methylcarbamic acid tert-butylester.

후처리

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate (20 ml)
  3. washThe combined organic layers were washed with a saturated solution of sodium hydrogencarbonate (30 ml)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customThe crude product was purified by flash chromatography on silica (50 g) with ethyl acetate

출처 및 근거

ORD 기록
ord-af906280f9e943d392048324366b1a01
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06013658

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