Piperidine → HCID 69621904, compound

HRID 1172153Notes

Reaction equation

HRID 1172153 reaction equation
[CH3:1][O:2][C:3]1[CH:53]=[CH:52][C:6]([C:7]([O:20][CH2:21][C@@H:22]([C@H:49]([CH3:51])[OH:50])[NH:23][C:24](=[O:48])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH:30]C(OCC2C3C(=CC=CC=3)C3C2=CC=CC=3)=O)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.N1CCCCC1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:20][CH2:21][C@@H:22]([C@H:49]([CH3:51])[OH:50])[NH:23][C:24](=[O:48])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH2:30])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:52][CH:53]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 69048213HCID 69048213, compound

Product 1

HCID 69621904HCID 69621904, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14 (9.1 g, 12.77 mmol) was dissolved in DMF (100 ml) containing piperidine (10 ml) and the reaction mixture was kept at RT for about 1 hour. The solvents were removed in vacuo and the residue purified by silica gel column chromatography using 1-10% gradient of methanol in dichloromethane to afford 15 as a syrup (4.46 g, 71%). 1H-NMR δ7.48-6.92 (m, 14H, aromatic), 6.16 (d, J=8.8, 1H, NH), 4.17 (m, 1H, H3 Thr), 4.02 (m, 1H, H2 Thr), 3.86 (s, 3H, OCH3), 3.50 (dd, J=9.7, J=4.4, 1H, H1 Thr), 3.37 (dd, J=9.7, J=3.4, 1H, H1′ THr), 2.78 (t, J=6.8, 2H, CH2CO Acp), 2.33 (t, J=7.6, 2H, CH2NH Acp), 1.76 (m, 2H, CH2 Acp), 1.56 (m, 2H, CH2 Acp), 1.50 (m, 2H, CH2 Acp), 1.21 (d, J=6.4, 3H, CH3). MS/ESI+ m/z 491.5 (M+H)+.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e39b2ff49e9d4141b8a3c0b60cdecaad
Source dataset
uspto-grants-2010_11
Patent number
US07833992B2

Reaction notes

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