Piperidine → HCID 53476207, compound

HRID 2204960Notes

Reaction equation

HRID 2204960 reaction equation
[C:1]([O:14][C@H:15]([CH2:64][O:65][C:66](=[O:78])[CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77])[CH2:16][S:17][CH2:18][C@H:19]([NH:46]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[C:20](=[O:45])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27]C(=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].N1CCCCC1>C(#N)C>[C:66]([O:65][CH2:64][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]([NH2:46])[C:20]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH2:27])=[O:45])(=[O:78])[CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 89428020HCID 89428020, compound

Product 1

HCID 53476207HCID 53476207, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (12R,16R)-12-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1-(9H-fluoren-9-yl)-3,11-dioxo-2-oxa-14-thia-4,10-diazaheptadecane-16,17-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 flash chromatography on an ISCO COMBIFLASH® system using a 0-20% MeOH (1% NH3)/DCM gradient to give (R)-3-((R)-2-amino-3-(5-aminopentylamino)-3-oxopropylthio)propane-1,2-diyl didodecanoate. 1H NMR (DMSO d-6): δ 7.91 (t, 1H), 5.09 (m, 1H), 4.26-4.32 (dd, 1H), 4.08-4.12 (m, 1H), 3.24-3.36 (m, 8H), 3.05-3.08 (m, 2H), 3.06 (m, 1H), 2.80 (m, 1H), 2.74 (t, 1H), 2.67 (dd, 1H), 2.60 (dd, 1H), 2.29-2.34 (q, 4H), 1.48-1.54 (m, 4H), 1.32-1.40 (m, 4H), 1.21-1.34 (m, 32H), 0.88 (t, 6H). LRMS [M+H]=645.1.

Workup

  1. concentrationAfter concentration
  2. customthe product was purified by flash chromatography on an ISCO COMBIFLASH® system

Sources & evidence

ORD record
ord-6a2db1143719472e8837408db0162ee1
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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