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Triethylamine → L-Proline, N-(methoxycarbonyl)-L-valyl-4-hydroxy-, methyl ester, (4R)-

HRID 1504308
ノート
印刷プレビュー

反応式

HRID 1504308 の反応式
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][NH:6]1)=[O:4].[CH3:11][O:12][C:13]([NH:15][C@@H:16]([CH:20]([CH3:22])[CH3:21])[C:17](O)=[O:18])=[O:14].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:17](=[O:18])[C@@H:16]([NH:15][C:13]([O:12][CH3:11])=[O:14])[CH:20]([CH3:22])[CH3:21])=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 7015125(4R)-4-Hydroxy-L-proline methyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid

生成物 1

HCID 58313116L-Proline, N-(methoxycarbonyl)-L-valyl-4-hydroxy-, methyl ester, (4R)-

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (2S,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester in dry DCM (200 mL) was added (S)-2-methoxycarbonylamino-3-methyl-butyric acid (10 g, 55 mmol), HATU (24 g, 63.25 mmol), and triethylamine (16.7 g, 165 mmol. The reaction mixture was stirred at RT overnight. DCM (200 mL) was added and the solution was washed with brine, dried, concentrated and purified by silica gel column chromatography (eluted with petroleum ether:EtOAc 10:1 to 1:4)) to give the title intermediate as a yellow oil (20 g). (m/z): [M+H]+ calcd for C13H22N2O6 303.15. found 303.1.

後処理

  1. washthe solution was washed with brine
  2. customdried
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography (eluted with petroleum ether:EtOAc 10:1 to 1:4))

出典と根拠

ORDレコード
ord-620faa5ba7d8450bb4339221b3c97eff
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09212168B2

反応ノート

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