Reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([NH:10][C:11](=[O:21])[CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=[N:8][CH:9]=1)=[O:4].[CH2:22](OC(C)C(O)=O)C1C=CC=CC=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C1COCC1.O>[CH3:1][O:2][C:3]([C:5]1[N:6]([NH:10][C:11](=[O:21])[CH:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:22])[CH:7]=[N:8][CH:9]=1)=[O:4]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of compound 2 (4.2 g, 29.7 mmol), 2-Benzyloxy-propionic acid (5.5 g, 29.7 mmol) and DIEA (10 mL) in a mixture of DMF (1 mL) and THF (50 mL) in ice-water bath was added HATU (13.5 g, 35.7 mmol). The resulting mixture was then stirred at ambient temperature overnight. Water (100 mL) was added. The mixture was extracted with ethyl acetate (300 mL×2). The combined organic phases were concentrated to give a crude residue, which was purified by chromatography on silica gel column (eluted with PE/EtOAc=1:1 to 1:3) to afford compound 9 (8.2 g, 91% yield) as brown oil. LC-MS: m/z 304 [M+H]+.
Workup
- extractionThe mixture was extracted with ethyl acetate (300 mL×2)
- concentrationThe combined organic phases were concentrated
- customto give a crude residue, which
- customwas purified by chromatography on silica gel column (eluted with PE/EtOAc=1:1 to 1:3)
Sources & evidence
- ORD record
- ord-efc87d032fbe4100bf345dd07e40e300
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434733B2
Linked notes
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