Piperidine → HCID 53476209, compound

HRID 2407865Notes

Reaction equation

HRID 2407865 reaction equation
C1C2C(COC([NH:18][C@@H:19]([CH2:38][S:39][CH2:40][C@H:41]([O:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH3:76])[CH2:42][O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[C:20](=[O:37])[NH:21][C@@H:22]([CH2:35][CH3:36])[C:23](=[O:34])[NH:24][C@@H:25]([C:31](=[O:33])[NH2:32])[CH2:26][CH2:27][C:28]([OH:30])=[O:29])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C(#N)C>[NH2:18][C@@H:19]([CH2:38][S:39][CH2:40][C@H:41]([O:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH3:76])[CH2:42][O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[C:20](=[O:37])[NH:21][C@@H:22]([CH2:35][CH3:36])[C:23](=[O:34])[NH:24][C@@H:25]([C:31](=[O:33])[NH2:32])[CH2:26][CH2:27][C:28]([OH:30])=[O:29]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86678270HCID 86678270, compound

Product 1

HCID 53476209HCID 53476209, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution (4R,7S,10R,14R)-10-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-carbamoyl-7-ethyl-14-(hexadecyloxy)-6,9-dioxo-16-oxa-12-thia-5,8-diazadotriacontan-1-oic acid in acetonitrile (0.1M) was stirred at room temperature. Piperidine (final conc. 20%) was then added and the reaction stirred for 30 min After concentration, the product was purified by flash chromatography on an ISCO COMBIFLASH® system using a 0-10% MeOH/DCM gradient to give (4R,7S,10R,14R)-10-amino-4-carbamoyl-7-ethyl-14-(hexadecyloxy)-6,9-dioxo-16-oxa-12-thia-5,8-diazadotriacontan-1-oic acid. 1H NMR (DMSO d-6): δ 12.12 (br, s, 1H), 8.56(d, 1H), 8.14 (t, 2H), 8.12 (d, 1H), 7.25 (s, 1H), 7.05 (s, 1H), 4.21-4.34 (m, 2H), 3.95-3.97 (m, 1H), 3.44-3.52 (m, 3H), 3.32-3.40 (m, 3H), 2.96 (dd, 1H), 2.66-2.78 (m, 4H), 2.19 (t, 2H), 1.89-1.98 (m, 2H), 1.67-1.76 (m, 4H), 1.56-1.64 (m, 2H), 1.42-1.50 (m, 4H), 1.21-1.28 (m, 48H), 0.83-0.89 (m, 9H). LRMS [M+H]=857.7.

Workup

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

Sources & evidence

ORD record
ord-671da6c63f3743a09822aee29ae11221
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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