(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid → HCID 71090133, compound

HRID 716817Notes

Reaction equation

HRID 716817 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.CN(C(=[N+](C)C)ON1C2=NC=CC=C2N=N1)C.[CH3:39][C:40]1([CH3:57])[C:48]2[C:43](=[CH:44][CH:45]=[C:46]([O:49][C:50]3[N:55]=[CH:54][C:53]([NH2:56])=[CH:52][CH:51]=3)[CH:47]=2)[CH2:42][O:41]1>CN(C=O)C>[CH3:39][C:40]1([CH3:57])[C:48]2[C:43](=[CH:44][CH:45]=[C:46]([O:49][C:50]3[N:55]=[CH:54][C:53]([NH:56][C:10]([C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][CH3:14])=[O:12])=[CH:52][CH:51]=3)[CH:47]=2)[CH2:42][O:41]1

Participants

5

Reactant 3

HCID 2755936(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71090134HCID 71090134, compound2×

Product 1

HCID 71090133HCID 71090133, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (2R)-2-(tert-butoxycarbonylamino)butanoic acid (19.8 mg, 0.097 mmol) in dry DMF (1 mL) N-ethyl-N-isopropyl-propan-2-amine (0.27 ml, 0.16 mmol) and then [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylene]-dimethyl-ammonium hexafluorophosphate (35.60 mg, 0.094 mmol) were added and the reaction mixture was stirred for 15 minutes at room temperature. A solution of 6-[(3,3-dimethyl-1H-isobenzofuran-5-yl)oxy]pyridin-3-amine (Intermediate 45, 20 mg, 0.0780 mmol) in DMF (0.5000 mL) was added and the reaction mixture was stirred overnight at the same temperature. The reaction was quenched with brine (5 ml) and extracted with ethyl acetate (2×10 ml). The organic layer was dried (Na2SO4), filtered and evaporated and the residue was purified by flash chromatography (Biotage system) on silica gel using a SNAP 10 g as column and cyclohexane/ethyl acetate from 100:0 to 50:50 as eluent affording the title compound (25 mg) as white solid.

Workup

  1. stirringthe reaction mixture was stirred overnight at the same temperature
  2. customThe reaction was quenched with brine (5 ml)
  3. extractionextracted with ethyl acetate (2×10 ml)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue was purified by flash chromatography (Biotage system) on silica gel using a SNAP 10 g as column and cyclohexane/ethyl acetate from 100:0 to 50:50 as eluent

Sources & evidence

ORD record
ord-33f8614617bb4d7fa078076c5d850303
Source dataset
uspto-grants-2015_11
Patent number
US09193704B2

Reaction notes

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