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

HRID 348840ノート

反応式

HRID 348840 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ab0ff06d0f5e4305824e291ca02fb3a4
出典データセット
uspto-grants-2007_02
特許番号
US07176242B2

反応ノート

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