Diethyl Ether → Azepane-1-carboxylic acid {1-[2-(4-benzyloxy-phenyl)-1-tert-butoxymethyl-ethylcarbamoyl]-3-methyl-butyl}-amide

HRID 278877노트

반응식

HRID 278877 반응식
[N:1]1([C:8]([NH:10][C@@H:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:12]([OH:14])=O)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN1CCOCC1.[CH2:26]([O:33][C:34]1[CH:48]=[CH:47][C:37]([CH2:38][C@H:39]([NH2:46])[CH2:40][O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[CH:36][CH:35]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(OCC)C>CN(C)C=O>[CH2:26]([O:33][C:34]1[CH:35]=[CH:36][C:37]([CH2:38][CH:39]([NH:46][C:12]([CH:11]([NH:10][C:8]([N:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]2)=[O:9])[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:14])[CH2:40][O:41][C:42]([CH3:44])([CH3:43])[CH3:45])=[CH:47][CH:48]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 79724-MethylmorpholineHCID 7530182(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acidHCID 12040965(s)-1-(4-Benzyloxy-benzyl)-2-tert-butoxy-ethylamine

생성물 1

HCID 18711790Azepane-1-carboxylic acid {1-[2-(4-benzyloxy-phenyl)-1-tert-butoxymethyl-ethylcarbamoyl]-3-methyl-butyl}-amide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
3 °C

실험 절차

A 3° C. solution of 106 mg (0.41 mmol) (S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid (Example 1, Step B) and 0.137 mL (0.41 mmol) 4-methylmorpholine in 2 mL N,N-dimethylformamide was treated with 165 mg (0.44 mmol) O-benzotriazol-1-yl-N,N,N′,N′-bis(tetramethylene)uranium hexafluorophosphate (Novabiochem, La Jolla, Calif.), and stirred for 30 minutes, at which time a solution of (S)-1-(4-benzyloxy-benzyl)-2-tert-butoxy-ethylamine in 3 mL dimethylformamide was added and the mixture stirred at 3° C. for 40 minutes. The clear solution was poured into 15 mL diethyl ether and washed successively with 15 mL of each of the following: 5% aqueous HCl, brine, saturated aqueous NaHCO3, brine (twice) then dried over anhydrous magnesium sulfate. The solvent was removed in vacuo affording 180 mg of white solid, which was recrystallized from hexane to give 116 mg (51%) of the title compound as a white solid; mp 98-99° C.

후처리

  1. additionwas added
  2. washwashed successively with 15 mL of each of the following: 5% aqueous HCl, brine, saturated aqueous NaHCO3, brine (twice)
  3. dry with materialthen dried over anhydrous magnesium sulfate
  4. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-ecfb45e40f6144f195f45fa8ae1a7811
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362174B1

반응 노트

불러오는 중…