Toluene → HCID 86678299, compound

HRID 2407912Notes

Reaction equation

C1C2C(COC([NH:18][C@@H:19]([CH2:33][S:34][CH2:35][C@H:36]([O:52][C:53](=[O:65])[CH2:54][CH2:55][CH2:56][CH2:57]CCCCCCC)[CH2:37][O:38][C:39](=[O:51])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[C:20]([NH:22][CH2:23][CH2:24][CH2:25][C:26]([P:29](=[O:32])([O-:31])[O-:30])([F:28])[F:27])=[O:21])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCC[CH2:68][CH2:67]1.[C:72]1([CH3:78])[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1.[C:79](#N)[CH3:80]>>[NH2:18][C@@H:19]([CH2:33][S:34][CH2:35][C@H:36]([O:52][C:53](=[O:65])[CH2:54][CH2:55][CH2:56][CH2:57][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:72][CH3:78])[CH2:37][O:38][C:39](=[O:51])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[C:20]([NH:22][CH2:23][CH2:24][CH2:25][C:26]([P:29](=[O:32])([O:30][CH2:79][CH3:80])[O:31][CH2:67][CH3:68])([F:28])[F:27])=[O:21]

Participants

Reactant 4

HCID 1140Toluene

HCID 6342Acetonitrile

HCID 8082Piperidine

HCID 86678300HCID 86678300, compound

Product 1

HCID 86678299HCID 86678299, compound

Conditions

Temperature: 25 °C

Procedure

To a solution of diethyl (4-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((R)-2,3-bis(dodecanoyloxy)propylthio)propanamido)-1,1-difluorobutylphosphonate (1 eq) was added 20% piperidine (50 eq) in acetonitrile. The resulting mixture was stirred at 25° C. until the deprotection completed. To the mixture was added toluene and then concentrated en vaccuo. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 100% EtOAc then 0-10% MeOH/DCM to give the product as a colorless oil.

Workup

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

Sources & evidence

ORD record: ord-391a3f314f464bb49b0d0613037c79b9
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08808703B2

Reaction notes

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