Diisopropylethylamine → Methyl 3-(2-{3-[({(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}amino)carbonyl]phenyl}-1,3-oxazol-5-yl)propanoate

HRID 14093

反応式

HRID 14093 の反応式
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][C:6]1[O:10][C:9]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=O)=[N:8][CH:7]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.[NH2:56][C@@H:57]([CH2:71][C:72]1[CH:77]=[C:76]([F:78])[CH:75]=[C:74]([F:79])[CH:73]=1)[C@H:58]([OH:70])[CH2:59][NH:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[C:64]([CH2:68][CH3:69])[CH:63]=1>C(Cl)Cl.CN(C=O)C>[F:78][C:76]1[CH:77]=[C:72]([CH:73]=[C:74]([F:79])[CH:75]=1)[CH2:71][C@H:57]([NH:56][C:14]([C:13]1[CH:12]=[C:11]([C:9]2[O:10][C:6]([CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:20])=[CH:7][N:8]=2)[CH:19]=[CH:18][CH:17]=1)=[O:16])[C@H:58]([OH:70])[CH2:59][NH:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[C:64]([CH2:68][CH3:69])[CH:63]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 210856913-[5-(3-Methoxy-3-oxopropyl)-1,3-oxazol-2-yl]benzoic acidHCID 57487281(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol dihydrochloride

生成物 1

HCID 57511988Methyl 3-(2-{3-[({(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}amino)carbonyl]phenyl}-1,3-oxazol-5-yl)propanoate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

3-[5-(3-Methoxy-3-oxopropyl)-1,3-oxazol-2-yl]benzoic acid (285 mg, 1.0 mmol) is dissolved in methylene chloride (5 mL) and DMF (5 mL), and diisopropylethylamine (695 μL, 4.0 mmol), HATU (472 g, 1.2 mmol), and (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol dihydrochloride prepared by the method of Example SP-272 (448 mg, 1.1 mmol) are added. The reaction stirred at room temperature 1 h. The reaction is partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 8% methanol/chloroform) provides the title compound. ESI MS m/z 591.9 [M+H]+.

後処理

  1. additionare added
  2. customThe reaction is partitioned between ethyl acetate and saturated sodium bicarbonate
  3. washThe organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography (silica, 8% methanol/chloroform)

出典と根拠

ORDレコード
ord-d7a5b13e893c4516a9442bb6bce35920
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

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