Veratrylamine → HCID 67495123, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[C:8]([CH:12]=1)[C:9]([OH:11])=O)([O-:3])=[O:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:53]([NH2:64])[C:54]1[CH:63]=[CH:62][C:59]([O:60][CH3:61])=[C:56]([O:57][CH3:58])[CH:55]=1>>[CH3:58][O:57][C:56]1[CH:55]=[C:54]([CH:63]=[CH:62][C:59]=1[O:60][CH3:61])[CH2:53][NH:64][C:9](=[O:11])[C:8]1[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[NH:13][CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1Participants
Procedure
A mixture of 5.8 g of the compound obtained in Step 6.1, 7.02 g of DIEA and 12.38 g of HBTU is stirred for 30 minutes at room temperature. 4.37 g of veratrylamine are then added and the resulting mixture is stirred overnight at room temperature. The resulting mixture is evaporated under reduced pressure and the residue is taken up in EtOAc. This solution is washed with water and then sequentially with 1N HCl solution, with water, with saturated NaHCO3 solution, with water and with saturated NaCl solution. The resulting solution is dried over Na2SO4 and filtered, and the solvent is evaporated off under reduced pressure. The residue is chromatographed on silica gel, eluting with an EtOAc/heptane mixture from (50/50, v/v) to (70/30, v/v) to give 7.7 g of the expected product.
Workup
- stirringthe resulting mixture is stirred overnight at room temperature
- customThe resulting mixture is evaporated under reduced pressure
- washThis solution is washed with water
- dry with materialThe resulting solution is dried over Na2SO4
- filtrationfiltered
- customthe solvent is evaporated off under reduced pressure
- customThe residue is chromatographed on silica gel
- washeluting with an EtOAc/heptane mixture from (50/50
Sources & evidence
- ORD record
- ord-216b4b71aa8a48e9876208860a8413c5
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722659B2
Reaction notes
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