HCID 117642440, compound → HCID 89625037, compound

HRID 1507741Notes

Reaction equation

HRID 1507741 reaction equation
C([O:8][C:9]1[C:13]([O:14][CH2:15][O:16][P:17]([O:27]CC2C=CC=CC=2)([O:19]CC2C=CC=CC=2)=[O:18])=[C:12]([C:35](=[O:39])[N:36]([CH3:38])[CH3:37])[N:11]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)[C:10]=1[C:48]([O:50][CH2:51][CH3:52])=[O:49])C1C=CC=CC=1>CO.[Pd]>[CH3:38][N:36]([CH3:37])[C:35]([C:12]1[N:11]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)[C:10]([C:48]([O:50][CH2:51][CH3:52])=[O:49])=[C:9]([OH:8])[C:13]=1[O:14][CH2:15][O:16][P:17]([OH:19])([OH:27])=[O:18])=[O:39]

Participants

4

Reactant 1

HCID 117642440HCID 117642440, compound

Product 1

HCID 89625037HCID 89625037, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ethyl 3-(benzyloxy)-4-(((bis(benzyloxy)phosphoryl)oxy)methoxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (42) (2.17 g, 2.99 mmol) in MeOH (20 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, the residue was taken up in water (50 mL) and washed with EtOAc (50 mL), the organic layer was washed with water (2×50 mL) and the combined aqueous layers were freeze-dried to afford ethyl 5-(dimethylcarbamoyl)-3-hydroxy-1-(4-methoxyphenyl)-4-((phosphonooxy)methoxy)-1H-pyrrole-2-carboxylate (UL1-109) (720 mg, 52%) as a white solid: m/z 459 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.14-7.05 (m, 2H), 6.93-6.85 (m, 2H), 5.35-5.23 (br m, 2H), 3.99 (q, J=7.2 Hz, 2H), 3.77 (s, 3H), 2.73 (s, 3H), 2.70 (s, 3H), 1.02 (t, J=7.2 Hz, 3H).

Workup

  1. customat 40° C.
  2. concentrationThe output was concentrated in vacuo
  3. washwashed with EtOAc (50 mL)
  4. washthe organic layer was washed with water (2×50 mL)
  5. customthe combined aqueous layers were freeze-dried

Sources & evidence

ORD record
ord-0a7b7853db574119a187b27123b71e86
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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