1,2-Dichloroethane → N1-((1S,2R)-1-benzyl-3-{[3-(2,4-dimethylphenyl)propyl]amino}-2-hydroxypropyl)-5-methyl-N3,N3-dipropylisophthalamide

HRID 348842

反応式

HRID 348842 の反応式
F[C:2](F)(F)C(O)=O.[NH2:8][C@@H:9]([CH2:23][C:24]1[CH:29]=[C:28](F)[CH:27]=[C:26](F)[CH:25]=1)[C@H:10]([OH:22])[CH2:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16](OC)[CH:15]=1.[CH2:32]([N:35]([CH2:48][CH2:49][CH3:50])[C:36]([C:38]1[CH:39]=[C:40]([CH:44]=[C:45]([CH3:47])[CH:46]=1)[C:41]([OH:43])=O)=[O:37])[CH2:33][CH3:34].[CH:51]1[CH:52]=CC2N(O)N=NC=2[CH:56]=1.CN1CCOCC1.C(Cl)CCl>C(Cl)Cl>[CH2:23]([C@H:9]([NH:8][C:41](=[O:43])[C:40]1[CH:44]=[C:45]([CH3:47])[CH:46]=[C:38]([C:36]([N:35]([CH2:32][CH2:33][CH3:34])[CH2:48][CH2:49][CH3:50])=[O:37])[CH:39]=1)[C@H:10]([OH:22])[CH2:11][NH:12][CH2:13][CH2:14][CH2:19][C:18]1[CH:17]=[CH:16][C:15]([CH3:2])=[CH:56][C:51]=1[CH3:52])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 113913935-methyl-N,N-dipropylisophthalamic acidHCID 69869154(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol Trifluoroacetate

生成物 1

HCID 68608870N1-((1S,2R)-1-benzyl-3-{[3-(2,4-dimethylphenyl)propyl]amino}-2-hydroxypropyl)-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 (2R,3S)-3-amino-1-{[3-(2,4-dimethylphenyl)propyl]amino}-4-phenyl-2-butanol hydrochloride (VIII, 163 mg, 0.411 mmol), 3-[(dipropylamino)carbonyl]-5-methylbenzoic acid (Ix, 108 mg, 0.411 mmol), HOBt (55 mg, 0.411 mmol), and N-methylmorpholine (133 mg, 1.32 mmol) in methylene chloride (5 mL) is added EDC (142 mg, 0.740 mmol). The reaction mixture is stirred overnight and then partitioned between ethyl acetate and water. The organic phase is washed with hydrochloric acid (1 N), saturated sodium bicarbonate, saline, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica; methylene chloride/methanol/ammonium hydroxide, 95/5/1) gives the title compound, IR (ATR): 3299, 2930 and 1614 cm−1; APCI-MS (m/z) [M+H]+=572.

後処理

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase is washed with hydrochloric acid (1 N), saturated sodium bicarbonate, saline
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography (silica; methylene chloride/methanol/ammonium hydroxide, 95/5/1)

出典と根拠

ORDレコード
ord-746cbb4becf04897acfb9a29c9a540da
出典データセット
uspto-grants-2007_02
特許番号
US07176242B2

関連ノート

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