Reaction equation
C([N:4](C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[Cl-].[NH4+].[C:45]([O:49][C:50]([NH:52][C:53]1[CH:57]=[CH:56][O:55][C:54]=1[C:58]([OH:60])=O)=[O:51])([CH3:48])([CH3:47])[CH3:46].Cl>CN(C=O)C>[NH2:4][C:58]([C:54]1[O:55][CH:56]=[CH:57][C:53]=1[NH:52][C:50](=[O:51])[O:49][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:60]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
Diisopropylethylamine (14.75 mL) was added to a suspension of PyBOP (10.4 g), ammonium chloride (1.81 g) and 3-[(tert-butoxycarbonyl)amino]-2-furoic acid (Intermediate 81) (3.83 g) in DMF (50 mL). The resulting mixture was stirred at ambient temperature for 90 minutes, poured into 0.4 M HCl (250 mL) and extracted into DCM (3×100 mL). The combined organics were washed with water (80 mL) and brine (80 mL), dried (MgSO4), and evaporated The product was purified by flash chromatography on silica, eluting with 20-70% EtOAc in isohexane to afford the title compound as a white solid (3.38 g, 89%);
Workup
- extractionextracted into DCM (3×100 mL)
- washThe combined organics were washed with water (80 mL) and brine (80 mL)
- dry with materialdried (MgSO4)
- customevaporated The product
- customwas purified by flash chromatography on silica
- washeluting with 20-70% EtOAc in isohexane
Sources & evidence
- ORD record
- ord-fc69a7ca2cf04a67bc09dcf34db3ae30
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07427616B2
Linked notes
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