HCID 89610615, compound → HCID 89610465, compound

HRID 1507696Notes

Reaction equation

HRID 1507696 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([C:22](=[O:26])[N:23]([CH3:25])[CH3:24])[N:11]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:10]=1C([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([NH+](CC)CC)C>C(O)(=O)C>[CH2:15]([O:14][C:13]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][N:11]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:12]=1[C:22]([N:23]([CH3:24])[CH3:25])=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 89610615HCID 89610615, compound

Product 1

HCID 89610465HCID 89610465, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of triethylammonium 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (7) (3.5 g, 6.70 mmol) in acetic acid (100 mL) was stirred at RT for 4 h and then 110° C. for 1 h. The volatiles were removed in vacuo and the crude material partitioned between EtOAc (100 mL) and 1M NaOH (aq.) (20 mL)/brine (50 mL), the organic layer was then dried (MgSO4), filtered and concentrated in vacuo to afford 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-N,N-dimethyl-1H-pyrrole-2-carboxamide (9) (3.05 g, 100%) as a yellow oil: m/z 457 (M+H)+ (ES+).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe crude material partitioned between EtOAc (100 mL) and 1M NaOH (aq.) (20 mL)/brine (50 mL)
  3. dry with materialthe organic layer was then dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad3d19d9e77846d2ac6d72c67e2e9413
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

Loading…