Piperidine → diethyl((14R,18R)-14-amino-18-dodecanamido-13-oxo-3,6,9,20-tetraoxa-16-thia-12-azadotriacontyl)phosphonate

HRID 2205036Notes

Reaction equation

C1C2C(OC(=O)[N:16](C)[C@@H:17]([CH2:40][S:41][CH2:42][C@H:43]([NH:58][C:59](=[O:71])[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH3:70])[CH2:44][O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[C:18](=[O:39])[NH:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][P:31]([O:36][CH2:37][CH3:38])([O:33][CH2:34][CH3:35])=[O:32])C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C1COCC1.CN(C=O)C>[CH2:34]([O:33][P:31]([CH2:30][CH2:29][O:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][NH:19][C:18](=[O:39])[C@@H:17]([NH2:16])[CH2:40][S:41][CH2:42][C@H:43]([NH:58][C:59](=[O:71])[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH3:70])[CH2:44][O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])(=[O:32])[O:36][CH2:37][CH3:38])[CH3:35]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of ((9H-fluoren-9-yl)methyl((14R,18R)-1-(diethoxyphosphoryl)-18-dodecanamido-13-oxo-3,6,9,20-tetraoxa-16-thia-12-azadotriacontan-14-yl)carbamate (1 eq) was added 20% piperidine (50 eq) in 4:1 THF/DMF. The resulting solution was stirred for 15 minutes at 25° C. and then concentrated en vaccuo. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-10% MeOH/DCM to give the title product as a white solid.

Workup

concentrationconcentrated en vaccuo
customThe crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record: ord-da2d59a98fd34927bdcea1aae88fd9f2
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365506B2

Reaction notes

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