1-Hydroxybenzotriazole → (S)-3-chloro-N-(4-hydroxy-1-(4-(2-(1-(hydroxyimino)ethyl)-1-methyl-1H-imidazol-4-yl)phenyl)butan-2-yl)-4-isopropoxybenzamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[O:33][CH:34]([CH3:36])[CH3:35])[C:5]([NH:7][C@H:8]([CH2:27][CH2:28][OH:29])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[C:18]([C:22](=[N:24][O:25]C)[CH3:23])[N:19]([CH3:21])[CH:20]=2)=[CH:12][CH:11]=1)=[O:6].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.Cl.CNOC.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[O:33][CH:34]([CH3:36])[CH3:35])[C:5]([NH:7][C@H:8]([CH2:27][CH2:28][OH:29])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[N:17]=[C:18]([C:22](=[N:24][OH:25])[CH3:23])[N:19]([CH3:21])[CH:20]=2)=[CH:14][CH:15]=1)=[O:6]Participants
7
Reactant 5
HCID 757711-Hydroxybenzotriazole
HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)
HCID 81531Diisopropylethylamine
HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 86604767(S)-3-chloro-N-(4-hydroxy-1-(4-(2-(1-(methoxyimino)ethyl)-1-methyl-1H-imidazol-4-yl)phenyl)butan-2-yl)-4-isopropoxybenzamideProduct 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2 (1.49 g, 2.29 mmol), HBTU (1.3 g, 3.44 mmol), HOBt (530 mg, 3.44 mmol), and N,O-dimethylhydroxylamine HCl salt (340 mg, 3.44 mmol) in DMF (20 mL) was added DIEA (785 uL, 4.58 mmol). The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated. The resulting residue was purified using silica gel (Hexanes/EtOAc=1:3) to give pure compound 3 (1.20 g, 78%) as an off-white, foamy solid.
Workup
- concentrationThe reaction mixture was concentrated
- customThe resulting residue was purified
Sources & evidence
- ORD record
- ord-36b5e31a965d48458d949bbabbaf21cc
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07618981B2
Reaction notes
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