Triethylamine → t-Butyl 2-{3-[4-(methoxycarbonyl)phenoxy]-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-5-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate

HRID 909494Notes

Reaction equation

HRID 909494 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:14]2[N:15]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:16]([C:19]3[S:20][CH:21]=[CH:22][N:23]=3)=[CH:17][CH:18]=2)[CH:5]=[C:6]([O:8][C@@H:9]([CH3:13])[CH2:10][O:11][CH3:12])[CH:7]=1.[CH3:31][O:32][C:33]([C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)=[O:34].C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:31][O:32][C:33]([C:35]1[CH:40]=[CH:39][C:38]([O:1][C:2]2[CH:3]=[C:4]([C:14]3[N:15]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[C:16]([C:19]4[S:20][CH:21]=[CH:22][N:23]=4)=[CH:17][CH:18]=3)[CH:5]=[C:6]([O:8][C@@H:9]([CH3:13])[CH2:10][O:11][CH3:12])[CH:7]=2)=[CH:37][CH:36]=1)=[O:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343694-Methoxycarbonylphenylboronic acidHCID 66681373t-Butyl 2-{3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-5-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate

Product 1

HCID 66683331t-Butyl 2-{3-[4-(methoxycarbonyl)phenoxy]-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-5-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylateYield 46%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

t-Butyl 2-{3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-5-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate (117 mg, 0.272 mmol) synthesized in Example (38d) was dissolved in dichloromethane (20 mL), and 4-methoxycarbonylphenyl boronic acid (100 mg, 0.556 mmol), copper (II) acetate (80 mg, 0.440 mmol), triethylamine (0.20 mL, 1.435 mmol) and molecular sieves 4A (100 mg) were added, followed by stirring at room temperature for 3 days under nitrogen atmosphere. The deposit of this reaction solution was Celite filtered. This mother liquor was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=15%-25%) to afford the desired compound (70 mg, yield 46%) as a yellow oil.

Workup

  1. filtrationfiltered
  2. distillationThis mother liquor was distilled off under reduced pressure
  3. customthe resulting residue was purified
  4. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=15%-25%)

Sources & evidence

ORD record
ord-9446027ffc4a4853a277b0d66616ce4f
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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