Triethylamine → HCID 86699927, compound
Reaction equation
CCN(CC)CC.[OH:8][C@@H:9]([CH3:28])[C@@H:10]([NH:14][C:15]([O:17][C:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2)=[O:16])[C:11]([OH:13])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH3:28][C@H:9]1[C@@H:10]([NH:14][C:15](=[O:16])[O:17][C:18]23[CH2:27][CH:22]4[CH2:21][CH:20]([CH2:26][CH:24]([CH2:23]4)[CH2:25]2)[CH2:19]3)[C:11](=[O:13])[O:8]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In a two necked round bottom flask, Et3N (0.34 ml, 2.42 mmol) was added to a solution of (2R,3S)-3-hydroxy-2-{[(tricyclo[3.3.1.13,7]dec-1-yloxy)carbonyl]amino}butanoic acid (0.240 g, 0.81 mmol) in dry CH2Cl2 (12 mL) under argon. After cooling at 0° C., HBTU (0.459 g, 1.21 mmol) was added and the mixture stirred 3 h at 0° C., then 16 h at rt. The obtained solid was filtered-off and the solvent removed under vacuum. The crude mixture was purified by typical silica gel column chromatography, eluting with Cy/AcOEt (90:10). The resulting white solid (0.093 g) was further triturated with cyclohexane to afford the pure title compound (0.065 g, 29%) as white solid. MS (ESI) m/z: 278.31 [M−H]−. Rf=0.19 (Cy/AcOEt 9:1, detection: ninhydrin). FTIR (cm−1): 3338, 2912, 2854, 1828, 1688, 1533, 1457, 1342, 1253, 1120, 1069, 1020, 970, 886, 820. 1H-NMR (CDCl3): δ 1.46 (d, 3H); 1.66 (m, 6H); 2.09 (m, 4H); 2.18 (m, 5H); 4.84 (m, 1H); 5.14 (d, 1H); 5.40 (t, 1H).
Workup
- custom16 h
- customat rt
- customthe solvent removed under vacuum
- customThe crude mixture was purified by typical silica gel column chromatography
- washeluting with Cy/AcOEt (90:10)
- customThe resulting white solid (0.093 g) was further triturated with cyclohexane
Sources & evidence
- ORD record
- ord-3d4a16f5887145eaa7f597be5d45befa
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09353075B2
Reaction notes
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