Potassium Carbonate → HCID 89610318, compound

HRID 1507715Notes

Reaction equation

HRID 1507715 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH2:10]([O:17][C:18]1[C:22]([OH:23])=[C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:20]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[C:19]=1[C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:10]([O:17][C:18]1[C:22]([O:23][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:20]([C:29]2[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)[C:19]=1[C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 89610365HCID 89610365, compound

Product 1

HCID 89610318HCID 89610318, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 2-bromoacetate (0.55 ml, 3.41 mmol) was added dropwise to a stirred solution of diethyl 3-(benzyloxy)-4-hydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylate (23) (1.0 g, 2.28 mmol) and K2CO3 (0.63 g, 4.55 mmol) in DMF (20 mL). The reaction mixture was stirred at RT for 18 h, and partitioned between EtOAc (200 mL) and sat. NaHCO3 (aq.) (200 mL), the organic layer was separated and washed with sat. NaHCO3 (aq.) (2×200 mL), dried (MgSO4), filtered and solvents removed in vacuo to give a yellow oil. The residue was purified by silica gel chromatography (120 g, 0-20% EtOAc in isohexane) to afford diethyl 3-(benzyloxy)-4-(2-(tert-butoxy)-2-oxoethoxy)-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylate (UL2-028) (912 mg, 72%) as a pale yellow oil: m/z 554 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.49-7.44 (m, 2H), 7.43-7.31 (m, 3H), 7.15-7.08 (m, 2H), 6.94-6.88 (m, 2H), 5.12 (s, 2H), 4.59 (s, 2H), 4.02-3.94 (m, 4H), 3.79 (s, 3H), 1.40 (s, 9H), 1.02 (t, J=7.1 Hz, 3H), 0.97 (t, J=7.1 Hz, 3H).

Workup

  1. custompartitioned between EtOAc (200 mL) and sat. NaHCO3 (aq.) (200 mL)
  2. customthe organic layer was separated
  3. washwashed with sat. NaHCO3 (aq.) (2×200 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customsolvents removed in vacuo
  7. customto give a yellow oil
  8. customThe residue was purified by silica gel chromatography (120 g, 0-20% EtOAc in isohexane)

Sources & evidence

ORD record
ord-928b7207f4684f6c8e0a67f53f3faf9c
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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