Diisopropylethylamine → HCID 178459155, compound
Reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[N:2]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.[O:42]1[CH2:45][CH:44]([O:46][C:47](=[O:68])[C@@:48]([CH2:66][OH:67])([CH3:65])[CH2:49][C@H:50]([NH2:64])[CH2:51][C:52]2[CH:57]=[CH:56][C:55]([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[CH:54][CH:53]=2)[CH2:43]1>CN(C=O)C>[O:42]1[CH2:45][CH:44]([O:46][C:47](=[O:68])[C@@:48]([CH2:66][OH:67])([CH3:65])[CH2:49][C@H:50]([NH:64][C:6]([C:4]2[NH:3][N:2]=[N:1][CH:5]=2)=[O:8])[CH2:51][C:52]2[CH:57]=[CH:56][C:55]([C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=3)=[CH:54][CH:53]=2)[CH2:43]1Participants
6
Reactant 4
HCID 81531Diisopropylethylamine2×
HCID 1401204-Carboxy-1,2,3-triazole
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 68181152(2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid oxetan-3-yl esterProduct 1
Reagents, catalysts & solvents 1
Procedure
1,2,3-Triazole-4-carboxylic acid (0.0274 g, 0.242 mmol), DIPEA (169 μL, 969 μmol) and HATU (92 mg, 242 μmol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid oxetan-3-yl ester (89.5 mg, 242 μmol), predissolved in DMF (0.2 mL) and DIPEA (0.5 eq.). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The product was purified by preparative HPLC and lyophilized to yield the title compound (17 mg; purity 95%). MS m/z [M+H]+ calc'd for C25H28N4O5, 465.21. found 465.4.
Workup
- stirringThe resulting mixture was stirred for 15 minutes
- customthe reaction was quenched with AcOH
- customThe product was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-5eeb712df9064bb78b188b7c22e94f78
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853427B2
Reaction notes
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