HCID 71598927, compound → HCID 136252910, compound

HRID 1507729Notes

Reaction equation

HRID 1507729 reaction equation
C([O:8][C:9]1[C:13]([O:14]CC2C=CC=CC=2)=[C:12]([C:22]2[N:23]=[N:24][NH:25][N:26]=2)[N:11]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:10]=1[C:35]([O:37][CH2:38][CH3:39])=[O:36])C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[C:13]([OH:14])=[C:12]([C:22]2[N:23]=[N:24][NH:25][N:26]=2)[N:11]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)[C:10]=1[C:35]([O:37][CH2:38][CH3:39])=[O:36]

Participants

4

Reactant 1

HCID 71598927HCID 71598927, compound

Product 1

HCID 136252910HCID 136252910, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ethyl 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-5-(2H-tetrazol-5-yl)-1H-pyrrole-2-carboxylate (UL1-090) (85 mg, 0.16 mmol) in MeOH (6 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 crude material was dissolved in DCM (5 mL) and washed with 1M HCl (aq.), brine (5 mL), sat. NaHCO3 (aq.) (5 mL), the basic aqueous layer was acidified with 1M HCl (aq.) (5 mL) and washed with DCM (2×5 mL), the combined organics were dried (MgSO4), filtered and solvents removed in vacuo to afford ethyl 3,4-dihydroxy-1-(4-methoxyphenyl)-5-(2H-tetrazol-5-yl)-1H-pyrrole-2-carboxylate (UL1-089) (45 mg, 79%) as a white solid: m/z 346 (M+H)+ (ES+); 344 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 9.30 (br s, 1H), 8.67 (s, 1H), 7.10-7.05 (m, 2H), 6.87-6.81 (m, 2H), 4.02 (q, J=7.1 Hz, 2H), 3.76 (s, 3H), 0.99 (t, J=7.1 Hz, 3H).

Workup

  1. customat 40° C.
  2. concentrationThe output was concentrated in vacuo
  3. dissolutionThe crude material was dissolved in DCM (5 mL)
  4. washwashed with 1M HCl (aq.), brine (5 mL), sat. NaHCO3 (aq.) (5 mL)
  5. washwashed with DCM (2×5 mL)
  6. dry with materialthe combined organics were dried (MgSO4)
  7. filtrationfiltered
  8. customsolvents removed in vacuo

Sources & evidence

ORD record
ord-7d46786f491847549b6cdf4f38cb62ee
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

Loading…