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

HRID 14014

反応式

HRID 14014 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
22.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-82f4803aa6514f62ba3dc9893e2e51d8
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

読み込み中…