N-(tert-butoxycarbonyl)glycine → ethyl N-(tert-butoxycarbonyl)glycyl-3-(6-methoxy-2-pyridinyl)alaninate

HRID 1972661Notes

Reaction equation

HRID 1972661 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][C@@H:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH2:11])[CH:6]=[CH:5][CH:4]=1.[C:17]([NH:24][CH2:25][C:26](O)=[O:27])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[C:20]([O:19][C:17]([NH:24][CH2:25][C:26]([NH:11][C@H:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=1)=[O:27])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66582562HCID 66582562, compound

Product 1

HCID 66582662ethyl N-(tert-butoxycarbonyl)glycyl-3-(6-methoxy-2-pyridinyl)alaninateYield 72.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a 100-mL round-bottomed flask was added ethyl 3-(6-methoxy-2-pyridinyl)alaninate (1.045 g, 4.66 mmol), N-boc-glycine (0.898 g, 5.13 mmol, Aldrich, St. Louis, Mo.), HATU (2.126 g, 5.59 mmol, Aldrich, St. Louis, Mo.), and N,N-diisopropylethylamine (2.43 mL, 13.98 mmol, Aldrich, St. Louis, Mo.) in DMF (5 mL). The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with water (40 mL) and extracted with EtOAc (2×50 mL). The organic extract was washed with saturated 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 70% EtOAc/hexanes to give ethyl N-(tert-butoxycarbonyl)glycyl-3-(6-methoxy-2-pyridinyl)alaninate (1.29 g) as a colorless oil.

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. extractionThe organic extract
  3. washwas washed with saturated 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 70% EtOAc/hexanes

Sources & evidence

ORD record
ord-b98d832e090a4b76a78ce26124e3bcf4
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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