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

HRID 1972546
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HRID 1972546 반응식
[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]
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참가 물질

7

반응물 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)

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2dcd9ca70385444abfcc1629340b43f6
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08431563B2

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