Piperidine → HCID 53476207, compound

HRID 2407861Notes

Reaction equation

HRID 2407861 reaction equation
[C:1]([O:14][C@H:15]([CH2:71][O:72][C:73](=[O:85])[CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH3:84])[CH2:16][S:17][CH2:18][C@H:19]([NH:53]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[C:20](=[O:52])[NH:21][CH2:22][CH2:23][CH2:24]OCCCCOCCCNC(=O)OCC1C2C=CC=CC=2C2C1=CC=CC=2)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH:86]1CCC[CH2:88][CH2:87]1>C(#N)C>[C:73]([O:72][CH2:71][C@@H:15]([O:14][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:16][S:17][CH2:18][C@H:19]([NH2:53])[C:20]([NH:21][CH2:22][CH2:23][CH2:24][CH2:88][CH2:87][NH2:86])=[O:52])(=[O:85])[CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH3:84]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86678267HCID 86678267, compound

Product 1

HCID 53476207HCID 53476207, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (19R, 23R)-19-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1-(9H-fluoren-9-yl)-3,18-dioxo-2,8,13-trioxa-21-thia-4,17-diazatetracosane-23,24-diyl didodecanoate in acetonitrile (0.1M) was stirred at room temperature. Piperidine (final conc. 20%) was then added and the reaction stirred for 30 minutes. After concentration, the product was purified by mass triggered HPLC using a 50-100% MeCN in H2O (0.1% TFA) gradient to give (R)-3-((R)-2-amino-3-(5-aminopentylamino)-3-oxopropylthio)propane-1,2-diyl didodecanoate). 1H NMR (DMSO d-6): δ 8.49 (t, 1H), 5.12 (m, 1H), 4.26-4.32 (dd, 1H), 4.08-4.12 (m, 1H), 3.85 (t, 1H), 3.32-3.41 (m, 7H), 3.20 (m, 2H), 3.11 (m, 1H), 2.91 (dd, 1H), 2.82 (m, 4H), 2.73 (m, 1H), 2.52 (m, 2H), 2.29-2.34 (q, 4H), 1.71-1.79 (m, 2H), 1.62-1.68 (m, 2H), 1.49-1.52 (m, 8H), 1.21-1.34 (m, 32H), 1.18-1.21 (t, 2H), 0.88 (t, 6H). LRMS [M+H]=747.1.

Workup

  1. concentrationAfter concentration
  2. customthe product was purified by mass

Sources & evidence

ORD record
ord-6f5bd9e6670b44819ebb59373c860569
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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