Triethylamine → HCID 67390971, compound

HRID 1040459Notes

Reaction equation

HRID 1040459 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][O:15][C:16](=[O:25])[CH:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C=O)C>[CH3:14][O:15][C:16](=[O:25])[CH:17]([NH:24][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:13])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 85082Tert-butoxycarbonylalanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10909919Methyl 2-amino-2-(pyridin-2-YL)acetate

Product 1

HCID 67390971HCID 67390971, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (S)-2-tert-Butoxycarbonylamino-propionic acid (1.54 g, 8.12 mmol), Amino-pyridin-2-yl-acetic acid methyl ester (1.35 g, 8.12 mmol) and HATU (3.1 g, 8.12 mmol) was added the DMF (20 mL) and Et3N (2.26 ml, 16.20 mmol) and the solution was stirred for 2 h. The mixture was concentrated to remove most of the DMF was removed. The resulting oil was dissolved in EtOAc, washed with water, 0.1 N HCl aq., 1 N NaHCO3 aq., followed by Brine. The combined organics were dried over MgSO4, filtered, and concentrated in vacuo to provide ((S)-2-tert-Butoxycarbonylamino-propionylamino)-pyridin-2-yl-acetic acid methyl ester (2.7 g, 98%) as a yellow oil, m/z 338.61 [M+1]+

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove most of the DMF
  3. customwas removed
  4. dissolutionThe resulting oil was dissolved in EtOAc
  5. washwashed with water, 0.1 N HCl aq., 1 N NaHCO3 aq.
  6. dry with materialThe combined organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ab885b42c7994a54af42b776cd43bf3d
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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