HCID 117642516, compound → HCID 117642616, compound

HRID 1507753Notes

Reaction equation

HRID 1507753 reaction equation
C([O:8][P:9]([O:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][C:25]([CH3:83])([CH3:82])[C:26]([O:28][C:29]1[C:33]([O:34][C:35](=[O:63])[C:36]([CH3:62])([CH3:61])[CH2:37][O:38][CH2:39][CH2:40][CH2:41][O:42][P:43]([O:53]CC2C=CC=CC=2)([O:45]CC2C=CC=CC=2)=[O:44])=[C:32]([C:64]([O:66][CH2:67][CH3:68])=[O:65])[N:31]([C:69]2[CH:74]=[CH:73][C:72]([O:75][CH3:76])=[CH:71][CH:70]=2)[C:30]=1[C:77](=[O:81])[N:78]([CH3:80])[CH3:79])=[O:27])([O:11]CC1C=CC=CC=1)=[O:10])C1C=CC=CC=1>CO.[Pd]>[CH3:83][C:25]([CH3:82])([CH2:24][O:23][CH2:22][CH2:21][CH2:20][O:19][P:9]([OH:10])([OH:11])=[O:8])[C:26]([O:28][C:29]1[C:33]([O:34][C:35](=[O:63])[C:36]([CH3:61])([CH3:62])[CH2:37][O:38][CH2:39][CH2:40][CH2:41][O:42][P:43]([OH:45])([OH:53])=[O:44])=[C:32]([C:64]([O:66][CH2:67][CH3:68])=[O:65])[N:31]([C:69]2[CH:70]=[CH:71][C:72]([O:75][CH3:76])=[CH:73][CH:74]=2)[C:30]=1[C:77](=[O:81])[N:78]([CH3:79])[CH3:80])=[O:27]

Participants

4

Reactant 1

HCID 117642516HCID 117642516, compound

Product 1

HCID 117642616HCID 117642616, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(dimethylcarbamoyl)-5-(ethoxycarbonyl)-1-(4-methoxyphenyl)-1H-pyrrole-3,4-diyl bis(3-(3-((bis(benzyloxy)phosphoryl)oxy)propoxy)-2,2-dimethylpropanoate) (56) (37 mg, 0.03 mmol) in MeOH (4 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 40° C. under H2 (full H2 mode). The output was concentrated in vacuo to afford 2-(dimethylcarbamoyl)-5-(ethoxycarbonyl)-1-(4-methoxyphenyl)-1H-pyrrole-3,4-diyl bis(2,2-dimethyl-3-(3-(phosphonooxy)propoxy)propanoate) (UL1-118) (25 mg, 95%) as a white gum: m/z 825 (M+H)+ (ES+); 823 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 7.24-7.16 (m, 2H), 6.98-6.91 (m, 2H), 4.01 (q, J=7.1 Hz, 2H), 3.90-3.81 (m, 4H), 3.79 (s, 3H), 3.51-3.43 (m, 8H), 2.82 (s, 3H), 2.70 (s, 3H), 1.86-1.73 (m, 4H), 1.25 (s, 6H), 1.19 (s, 6H), 1.01 (t, J=7.1 Hz, 3H).

Workup

  1. customat 40° C.
  2. concentrationThe output was concentrated in vacuo

Sources & evidence

ORD record
ord-411b342a203e4acabe0ba90061e269c9
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

Loading…