Triethylamine → [(1S,2R)-2-tert-butoxy-1-(1-pyrimidin-2-yl-cyclopropylcarbamoyl)-propyl]-carbamic acid tert-butyl ester

HRID 1040499Notes

Reaction equation

HRID 1040499 reaction equation
[C:1]([O:5][C@H:6]([CH3:19])[C@H:7]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:8]([OH:10])=O)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.Cl.Cl.[N:53]1[CH:58]=[CH:57][CH:56]=[N:55][C:54]=1[C:59]1([NH2:62])[CH2:61][CH2:60]1>CN(C=O)C.O>[C:15]([O:14][C:12](=[O:13])[NH:11][C@H:7]([C:8](=[O:10])[NH:62][C:59]1([C:54]2[N:55]=[CH:56][CH:57]=[CH:58][N:53]=2)[CH2:61][CH2:60]1)[C@H:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH3:19])([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 7015770(2S,3R)-3-(tert-butoxy)-2-(((tert-butoxy)carbonyl)amino)butanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67390310HCID 67390310, compound

Product 1

HCID 67390977[(1S,2R)-2-tert-butoxy-1-(1-pyrimidin-2-yl-cyclopropylcarbamoyl)-propyl]-carbamic acid tert-butyl esterYield 81.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S,3R)-3-tert-butoxy-2-tert-butoxycarbonylamino-butyric acid (0.20 g, 0.72 mmol) in DMF (1 mL) was added HATU (0.27 g, 0.72 mmol), Et3N (0.30 mL, 2.2 mmol) and 1-pyrimidin-2-yl-cyclopropylamine dihydrochloride (0.15 g, 0.72 mmol.). The reaction was allowed to stir at RT for 24 h. The mixture was diluted with water and extracted with EtOAc (3×50 mL). The combined extracts were washed with satd NaHCO3, 2N HCl, water and brine. The solution was dried with MgSO4, filtered and concentrated to give [(1S,2R)-2-tert-butoxy-1-(1-pyrimidin-2-yl-cyclopropylcarbamoyl)-propyl]-carbamic acid tert-butyl ester (0.23 g, 0.59 mmol).

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined extracts were washed with satd NaHCO3, 2N HCl, water and brine
  3. dry with materialThe solution was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7e498d787faf4d8093d492d2cfb64de0
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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