HCID 117642836, compound → HCID 117642446, compound

HRID 1507758Notes

Reaction equation

HRID 1507758 reaction equation
C([O:8][P:9]([O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][C:27]([CH3:87])([CH3:86])[C:28]([O:30][C:31]1[C:35]([O:36][C:37](=[O:67])[C:38]([CH3:66])([CH3:65])[CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][P:47]([O:57]CC2C=CC=CC=2)([O:49]CC2C=CC=CC=2)=[O:48])=[C:34]([C:68](=[O:72])[N:69]([CH3:71])[CH3:70])[N:33]([C:73]2[CH:78]=[CH:77][C:76]([O:79][CH3:80])=[CH:75][CH:74]=2)[C:32]=1[C:81](=[O:85])[N:82]([CH3:84])[CH3:83])=[O:29])([O:11]CC1C=CC=CC=1)=[O:10])C1C=CC=CC=1>CO.[Pd]>[CH3:86][C:27]([CH3:87])([CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][P:9]([OH:10])([OH:11])=[O:8])[C:28]([O:30][C:31]1[C:35]([O:36][C:37](=[O:67])[C:38]([CH3:65])([CH3:66])[CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][P:47]([OH:49])([OH:57])=[O:48])=[C:34]([C:68](=[O:72])[N:69]([CH3:71])[CH3:70])[N:33]([C:73]2[CH:74]=[CH:75][C:76]([O:79][CH3:80])=[CH:77][CH:78]=2)[C:32]=1[C:81](=[O:85])[N:82]([CH3:83])[CH3:84])=[O:29]

Participants

4

Reactant 1

HCID 117642836HCID 117642836, compound

Product 1

HCID 117642446HCID 117642446, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2,5-bis(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-3,4-diyl bis(3-(2-(2-((bis(benzyloxy)phosphoryl)oxy)ethoxy)ethoxy)-2,2-dimethylpropanoate) (62) (278 mg, 0.22 mmol) in MeOH (112 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 45° C. under H2 (10 bar). The output was concentrated in vacuo to afford 2,5-bis(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-3,4-diyl bis(2,2-dimethyl-3-(2-(2-(phosphonooxy)ethoxy)ethoxy)propanoate) (UL1-121) (175 mg, 88%) as a light yellow oil: m/z 884 (M+H)+ (ES+); 882 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 7.11-7.09 (m, 2H), 6.97-6.95 (m, 2H), 3.91-3.87 (m, 4H), 3.78 (s, 3H), 3.58-3.50 (m, 16H), 2.89 (s, 6H), 2.76 (s, 6H), 1.19 (s, 12H).

Workup

  1. customat 45° C.
  2. concentrationThe output was concentrated in vacuo

Sources & evidence

ORD record
ord-0d318f98b47b4b56a99ad919a356f017
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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