1,2-Dichloroethane → N1-((1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-5-methyl-N3,N3-dipropylisophthalamide

HRID 348840노트

반응식

HRID 348840 반응식
C(OC[CH2:10][CH2:11][CH2:12][N:13]([CH2:26][CH2:27][CH3:28])[C:14]([C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[C:19]([OH:21])=O)=[O:15])C1C=CC=CC=1.F[C:30](F)(F)[C:31]([OH:33])=O.[NH2:36][C@@H:37]([CH2:51][C:52]1[CH:57]=[C:56](F)[CH:55]=[C:54](F)[CH:53]=1)[C@H:38]([OH:50])[CH2:39][NH:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([O:48][CH3:49])[CH:43]=1.C(N(CC)C(C)C)(C)C.[CH:69]1[CH:70]=[CH:71]C2N(O)N=N[C:73]=2[CH:74]=1.C(Cl)CCl>ClCCl>[CH2:31]([O:33][C:55]1[CH:56]=[CH:57][C:52]([CH2:51][C@H:37]([NH:36][C:19](=[O:21])[C:18]2[CH:22]=[C:23]([CH3:25])[CH:24]=[C:16]([C:14]([N:13]([CH2:12][CH2:11][CH3:10])[CH2:26][CH2:27][CH3:28])=[O:15])[CH:17]=2)[C@H:38]([OH:50])[CH2:39][NH:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([O:48][CH3:49])[CH:43]=2)=[CH:53][CH:54]=1)[C:30]1[CH:71]=[CH:70][CH:69]=[CH:74][CH:73]=1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 210856863-{[[4-(Benzyloxy)butyl](propyl)amino]carbonyl)-5-methylbenzoic acidHCID 69869154(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol Trifluoroacetate

생성물 1

HCID 68609943N1-((1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-5-methyl-N3,N3-dipropylisophthalamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred mixture of 3-[(dipropylamino)-carbonyl]-5-methylbenzoic acid (IX, 150 mg, 0.570 mmol), (2R,3S)-3-amino-4-[4-(benzyloxy)phenyl]-1-[(3-methoxybenzyl)amino]-2-butanol hydrochloride (VIII, 274 mg, 0.571 mmol), N,N-diisopropylethylamine (400 microliter, 2.28 mmol), and HOBt (116 mg, 0.857 mmol) in dichloromethane (10 mL) is added EDC (165 mg, 0.857 mmol). The resulting mixture is stirred at 20–25 degrees C. for 16 hours. The reaction mixture is partitioned between dichloromethane and water. The aqueous phase is separated and extracted with dichloromethane (3×15 mL). The combined organic phases are washed with water, dried (magnesium sulfate), and concentrated under reduced pressure. Purification by flash column chromatography (silica; dichloromethane/methanol/ammonium hydroxide, 97/3/0.05) gives N1-{(1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-5-methyl-N3,N3-dipropylisophthalamide, ESI-MS (m/z) [M+H]+=652.

후처리

  1. customThe reaction mixture is partitioned between dichloromethane and water
  2. customThe aqueous phase is separated
  3. extractionextracted with dichloromethane (3×15 mL)
  4. washThe combined organic phases are washed with water
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography (silica; dichloromethane/methanol/ammonium hydroxide, 97/3/0.05)

출처 및 근거

ORD 기록
ord-ab0ff06d0f5e4305824e291ca02fb3a4
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

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