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N-(tert-butoxycarbonyl)glycine → ethyl N-(tert-butoxycarbonyl)glycyl-3-methoxyphenylalaninate

HRID 1972546
ノート
印刷プレビュー

反応式

HRID 1972546 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[CH2:6][C@@H:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH2:8].[C:17]([O:21][C:22]([NH:24][CH2:25][C:26](O)=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>O.CN(C=O)C>[C:17]([O:21][C:22]([NH:24][CH2:25][C:26]([NH:8][C@H:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][C:5]1[CH:14]=[CH:15][CH:16]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 8027297ethyl (2S)-2-amino-3-(3-methoxyphenyl)propanoateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 66582631ethyl N-(tert-butoxycarbonyl)glycyl-3-methoxyphenylalaninate
収率 91.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a 100-mL round-bottomed flask was added ethyl 3-methoxyphenylalaninate (526 mg, 2.35 mmol), 2-(tert-butoxycarbonylamino)acetic acid (454 mg, 2.59 mmol, Sigma-Aldrich, St. Louis, Mo.), HATU (1.07 g, 2.82 mmol, Sigma-Aldrich, St. Louis, Mo.), Hünig's base (0.819 mL, 4.71 mmol) and DMF (5 mL). The reaction mixture was stirred at room temperature for 2 h then diluted with water (30 mL) and extracted with EtOAc (2×50 mL). The organic extract was washed with saturated aqueous NaCl (30 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as light-yellow oil. The crude product was purified by silica gel chromatography, eluting with 60% EtOAc in hexanes to give ethyl N-(tert-butoxycarbonyl)glycyl-3-methoxyphenylalaninate (822 mg).

後処理

  1. extractionextracted with EtOAc (2×50 mL)
  2. extractionThe organic extract
  3. washwas washed with saturated aqueous NaCl (30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customto give the crude material as light-yellow oil
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with 60% EtOAc in hexanes

出典と根拠

ORDレコード
ord-2dcd9ca70385444abfcc1629340b43f6
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08431563B2

反応ノート

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