Piperidine → HCID 89428566, compound

HRID 2204963Notes

Reaction equation

HRID 2204963 reaction equation
[C:1]([O:14][C@H:15]([CH2:97][O:98][C:99](=[O:111])[CH2:100][CH2:101][CH2:102][CH2:103][CH2:104][CH2:105][CH2:106][CH2:107][CH2:108][CH2:109][CH3:110])[CH2:16][S:17][CH2:18][C@H:19]([NH:79]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[C:20](=[O:78])[NH:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][NH:35][C:36](=[O:77])[CH:37]([CH2:56][S:57][C:58]([C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)([C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[NH:38]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:1]([O:14][C@H:15]([CH2:97][O:98][C:99](=[O:111])[CH2:100][CH2:101][CH2:102][CH2:103][CH2:104][CH2:105][CH2:106][CH2:107][CH2:108][CH2:109][CH3:110])[CH2:16][S:17][CH2:18][C@H:19]([NH2:79])[C:20](=[O:78])[NH:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][NH:35][C:36](=[O:77])[CH:37]([NH2:38])[CH2:56][S:57][C:58]([C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=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]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 89428323HCID 89428323, compound

Product 1

HCID 89428566HCID 89428566, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (23R,27R)-23-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1-(9H-fluoren-9-yl)-3,6,22-trioxo-5-(tritylthiomethyl)-2,11,14,17-tetraoxa-25-thia-4,7,21-triazaoctacosane-27,28-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 an initial gradient of 0-100% EtOAc, then 0-10% MeOH/DCM to give (22R,26R)-4,22-diamino-5,21-dioxo-1,1,1-triphenyl-10,13,16-trioxa-2,24-dithia-6,20-diazaheptacosane-26,27-diyl didodecanoate.

Workup

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

Sources & evidence

ORD record
ord-19ea7e1d001f4575b4e9d7cebcb43dcf
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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