HCID 89610295, compound → HCID 89610574, compound

HRID 1507721Notes

Reaction equation

HRID 1507721 reaction equation
C([O:8][P:9]([O:19][C:20]1[C:21]([OH:43])=[C:22]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:23]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C:24]=1[C:25](=[O:29])[N:26]([CH3:28])[CH3:27])([O:11]CC1C=CC=CC=1)=[O:10])C1C=CC=CC=1>CO.[Pd]>[CH3:28][N:26]([CH3:27])[C:25]([C:24]1[N:23]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C:22]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[C:21]([OH:43])[C:20]=1[O:19][P:9]([OH:10])([OH:11])=[O:8])=[O:29]

Participants

4

Reactant 1

HCID 89610295HCID 89610295, compound

Product 1

HCID 89610574HCID 89610574, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ethyl 4-((bis(benzyloxy)phosphoryl)oxy)-5-(dimethylcarbamoyl)-3-hydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (26) (225 mg, 0.37 mmol) in MeOH (10 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 30° C. under H2 (full H2 mode). The output was concentrated in vacuo to afford ethyl 5-(dimethylcarbamoyl)-3-hydroxy-1-(4-methoxyphenyl)-4-(phosphonooxy)-1H-pyrrole-2-carboxylate (UL1-070) (151 mg, 94%) as a pale yellow solid: m/z 429 (M+H)+ (ES+); 427 (M−H)− (ES−), 1H NMR (400 MHz, DMSO-d6) δ: 7.11-7.03 (m, 2H), 6.93-6.85 (m, 2H), 3.99 (q, J=7.1 Hz, 2H), 3.77 (s, 3H), 2.82 (s, 3H), 2.71 (s, 3H), 1.02 (t, J=7.1 Hz, 3H).

Workup

  1. customat 30° C.
  2. concentrationThe output was concentrated in vacuo

Sources & evidence

ORD record
ord-0e290ace3e1143758b490bd371c2b24f
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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