1,2-Dichloroethane → N1-{(1S,2R)-1-Benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl)-N3,N3-dipropyl-1,3,5-benzenetricarboxamide

HRID 14014

반응식

HRID 14014 반응식
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])=[O:14])[CH:12]=1)[C:7](O)=[O:8])=[O:3].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.FC(F)(F)C(O)=O.[NH2:50][C@@H:51]([CH2:65][C:66]1[CH:71]=[C:70](F)[CH:69]=[C:68](F)[CH:67]=1)[C@H:52]([OH:64])[CH2:53][NH:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[C:58]([O:62][CH3:63])[CH:57]=1>CN(C=O)C>[CH2:65]([C@H:51]([NH:50][C:7]([C:6]1[CH:5]=[C:4]([C:2]([NH2:1])=[O:3])[CH:12]=[C:11]([C:13]([N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])=[O:14])[CH:10]=1)=[O:8])[C@H:52]([OH:64])[CH2:53][NH:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[C:58]([O:62][CH3:63])[CH:57]=1)[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 223948913-Carbamoyl-5-dipropylcarbamoyl-benzoic acidHCID 69869154(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol Trifluoroacetate

생성물 1

HCID 44426032N1-{(1S,2R)-1-Benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl)-N3,N3-dipropyl-1,3,5-benzenetricarboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
22.5 °C

실험 절차

To a mixture of 3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoic acid (IX, PREPARATION 6, 0.18 g, 0.616 mmol) in dry DMF (16 mL) is added EDC (0.182 g, 0.9 mmol), HOBT (0.127 g, 0.9 mmol), triethylamine (0.062 g, 0.616 mol), and (2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol (VIII, EXAMPLE 175, 0.185 g, 0.616 mmol). The mixture is stirred at 20-25 degrees C. for 3 days. The mixture is partitioned between water and ethyl acetate. The phases are separated and the organic phase is washed three times with water. The organic phase is dried over anhydrous magnesium sulfate, filtered and concentrated. Column chromatography (silica gel, 75 mL; methanol/methylene chloride, 10/90) gives the title compound, IR (diffuse reflectance) 3306, 3301, 3270, 2962, 1676, 1667, 1663, 1645, 1638, 1627, 1615, 1550, 1537, 1450 and 1439 cm−1; NMR (CDCl3) δ 0.645, 0.968, 1.20, 1.43, 1.67, 2.8, 2.97, 3.38, 3.47, 3.73, 3.87, 4.31, 6.78, 6.91, 7.23, 7.72, 7.87, 8.22 and 8.43.

후처리

  1. customThe mixture is partitioned between water and ethyl acetate
  2. customThe phases are separated
  3. washthe organic phase is washed three times with water
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-82f4803aa6514f62ba3dc9893e2e51d8
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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