Piperidine → HCID 59404230, compound

HRID 56328Notes

Reaction equation

HRID 56328 reaction equation
[C:1]([O:5][C:6](=[O:88])[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][N:14]([CH2:74][C:75]1[N:76]([CH2:80][C:81](=[O:87])[O:82][C:83]([CH3:86])([CH3:85])[CH3:84])[CH:77]=[CH:78][N:79]=1)[CH2:15][CH2:16][CH2:17][CH2:18][C@@H:19]([C:38](=[O:73])[NH:39][CH2:40][CH2:41][CH2:42][CH2:43][C@@H:44]([C:66]([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:67])[NH:45][C:46](=[O:65])[NH:47][C@H:48]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[CH2:49][CH2:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[NH:20]C(=O)OCC1C2C=CC=CC=2C2C1=CC=CC=2)([CH3:4])([CH3:3])[CH3:2].N1CCCCC1>CN(C=O)C>[NH2:20][C@H:19]([C:38](=[O:73])[NH:39][CH2:40][CH2:41][CH2:42][CH2:43][C@@H:44]([C:66]([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:67])[NH:45][C:46](=[O:65])[NH:47][C@H:48]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[CH2:49][CH2:50][C:51]([O:53][C:54]([CH3:55])([CH3:56])[CH3:57])=[O:52])[CH2:18][CH2:17][CH2:16][CH2:15][N:14]([CH2:13][C:9]1[N:8]([CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:88])[CH:12]=[CH:11][N:10]=1)[CH2:74][C:75]1[N:76]([CH2:80][C:81]([O:82][C:83]([CH3:86])([CH3:85])[CH3:84])=[O:87])[CH:77]=[CH:78][N:79]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 59404257HCID 59404257, compound

Product 1

HCID 59404230HCID 59404230, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (5S,12S,16S)-tri-tert-butyl 5-(4-(bis((1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)butyl)-1-(9H-fluoren-9-yl)-3,6,14-trioxo-2-oxa-4,7,13,15-tetraazaoctadecane-12,16,18-tricarboxylate (84 mg, 0.069 mmol) in DMF (0.50 mL) was added piperidine (0.50 mL). The mixture was stirred at room temperature for 2 hrs. Solvent was evaporated under reduce pressure to afford a residue, which was purified by biotage eluting with 5% MeOH to 25% MeOH in DCM to afford (7S,14S,18S)-tri-tert-butyl 7-amino-1-(1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-2-yl)-2-((1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-2-yl)methyl)-8,16-dioxo-2,9,15,17-tetraazaicosane-14,18,20-tricarboxylate (59 mg, 86%). 1H NMR (400 MHz, CDCl3) 6.96 (d, J=0.8 Hz, 2H), 6.85 (d, J=0.8 Hz, 2H), 5.55 (brs, 1H), 5.43 (brs, 1H), 4.59 (s, 4H), 4.37-4.28 (m, 2H), 3.61 (s, 4H), 3.35-3.27 (m, 2H), 3.18-3.12 (m, 1H), 2.53 (t, J=7.4 Hz, 2H), 2.34-2.28 (m, 2H), 2.10-2.00 (m, 2H), 1.85-1.26 (m, 55H); MS (ESI), 503.0 (M/2+H)+.

Workup

  1. customSolvent was evaporated
  2. customto afford a residue, which
  3. customwas purified by biotage
  4. washeluting with 5% MeOH to 25% MeOH in DCM

Sources & evidence

ORD record
ord-66a13d75259a43fa969e508cc72955c4
Source dataset
uspto-grants-2016_09
Patent number
US09433594B2

Reaction notes

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