HCID 117642458, compound → HCID 89625044, compound

HRID 1507757Notes

Reaction equation

HRID 1507757 reaction equation
C([O:8][C:9]1[C:10]([O:32][CH2:33][O:34][P:35]([O:45]CC2C=CC=CC=2)([O:37]CC2C=CC=CC=2)=[O:36])=[C:11]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:12]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:13]=1[C:14](=[O:18])[N:15]([CH3:17])[CH3:16])C1C=CC=CC=1>CO.[Pd]>[CH3:17][N:15]([CH3:16])[C:14]([C:13]1[N:12]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:11]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:10]([O:32][CH2:33][O:34][P:35]([OH:37])([OH:45])=[O:36])[C:9]=1[OH:8])=[O:18]

Participants

4

Reactant 1

HCID 117642458HCID 117642458, compound

Product 1

HCID 89625044HCID 89625044, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ethyl 4-(benzyloxy)-3-(((bis(benzyloxy)phosphoryl)oxy)methoxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (61) (102 mg, 0.14 mmol) in MeOH (5 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 (full H2 mode). The output was concentrated in vacuo to afford ethyl 5-(dimethylcarbamoyl)-4-hydroxy-1-(4-methoxyphenyl)-3-((phosphonooxy)methoxy)-1H-pyrrole-2-carboxylate (UL1-115) (61 mg, 93%) as a white solid: m/z 459 (M+H)+ (ES+); 457 (M−H)− (ES−), 1H NMR (400 MHz, DMSO-d6) δ: 7.11-7.05 (m, 2H), 6.91-6.84 (m, 2H), 5.45 (d, J=16 Hz, 2H), 3.98 (q, J=7.1 Hz, 2H), 3.77 (s, 3H), 2.98 (br s, 3H) 2.74 (br s, 3H), 1.01 (t, J=7.0 Hz, 3H).

Workup

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

Sources & evidence

ORD record
ord-c26849cda8df4b3cbd14ec85921cbdea
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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