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

HRID 348842

반응식

HRID 348842 반응식
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

참가 물질

7

반응물 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

생성물 1

HCID 68608870N1-((1S,2R)-1-benzyl-3-{[3-(2,4-dimethylphenyl)propyl]amino}-2-hydroxypropyl)-5-methyl-N3,N3-dipropylisophthalamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-746cbb4becf04897acfb9a29c9a540da
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

연결된 노트

불러오는 중…