Triethylamine → HCID 53973617、化合物

HRID 1701043ノート

反応式

HRID 1701043 の反応式
[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]

参加物

10

反応物 6

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

生成物 1

HCID 53973617HCID 53973617、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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 lh 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.

後処理

  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

出典と根拠

ORDレコード
ord-30b95248d315432ca45c36858513c1a2
出典データセット
uspto-grants-2002_02
特許番号
US06350767B1

反応ノート

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