N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → HCID 58423379, compound

HRID 1398018Notes

Reaction equation

HRID 1398018 reaction equation
Cl.[N:2]1([C:8]2[C:13](/[CH:14]=[C:15]3/[C:16](=[O:21])[NH:17][C:18](=[O:20])[S:19]/3)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:22]([O:26][C:27]([NH:29][CH2:30][CH2:31][C:32](O)=[O:33])=[O:28])([CH3:25])([CH3:24])[CH3:23].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.CN(C=O)C>[O:20]=[C:18]1[NH:17][C:16](=[O:21])/[C:15](=[CH:14]/[C:13]2[C:8]([N:2]3[CH2:7][CH2:6][N:5]([C:32](=[O:33])[CH2:31][CH2:30][NH:29][C:27](=[O:28])[O:26][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:4][CH2:3]3)=[N:9][CH:10]=[CH:11][CH:12]=2)/[S:19]1

Participants

7

Reactant 4

HCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86657371HCID 86657371, compound

Product 1

HCID 58423379HCID 58423379, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A 50 mL vial was charged with a magnetic spin bar, (Z)-5-((2-(piperazin-1-yl)pyridin-3-yl)methylene)thiazolidine-2,4-dione hydrochloride (Example 89) (0.125 g, 0.38 mmol), 3-(tert-butoxycarbonylamino)propanoic acid (0.109 g, 0.57 mmol), DMF (1.912 ml), and diisopropylethylamine (0.334 ml, 1.91 mmol). With stirring, HATU (0.291 g, 0.76 mmol) was added and the reaction was warmed to 50° C. for 3 h. The reaction was then diluted with water and extracted with ethyl acetate (3×50 mL). The combined organic extract was dried with MgSO4, filtered through a bed of Celite, and conc. in vacuo to yield the product which was purified via silica gel chromatography (80 g) using ethyl acetate/hexanes (1:1) as eluent to provide the title compound as an off white solid. (0.080 g, 45.3%); m/z 462.

Workup

  1. additionA 50 mL vial was charged with a magnetic spin bar
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. extractionThe combined organic extract
  4. dry with materialwas dried with MgSO4
  5. filtrationfiltered through a bed of Celite
  6. customconc. in vacuo to yield the product which
  7. customwas purified via silica gel chromatography (80 g)

Sources & evidence

ORD record
ord-f9bad571fb0a4705a021138741bb7e71
Source dataset
uspto-grants-2014_12
Patent number
US08901307B2

Reaction notes

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