Acetic Acid Mixture with Hydrobromic Acid → HCID 58679100, compound

HRID 1442532Notes

Reaction equation

HRID 1442532 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22]CC3C=CC=CC=3)=[CH:18][C:17]=2[O:30]CC2C=CC=CC=2)=[C:14]([CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[C:13]2[S:44][C:45]([C:47]([O:49][CH3:50])=[O:48])=[CH:46][C:12]1=2)[C:2]1C=CC=CC=1.Br.C(O)(=[O:54])C>C(O)(=O)C>[C:1]([O:8][CH2:9][CH2:10][N:11]1[C:15]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=2[OH:30])=[C:14]([CH:38]2[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]2)[C:13]2[S:44][C:45]([C:47]([O:49][CH3:50])=[O:48])=[CH:46][C:12]1=2)(=[O:54])[CH3:2]

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 58679082HCID 58679082, compound

Product 1

HCID 58679100HCID 58679100, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 4-(2-benzyloxyethyl)-5-(2,4-bisbenzyloxyphenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (1.21 g, 1.77 mmol) in acetic acid (3 ml) was added 25% hydrogen bromide-acetic acid solution (3 ml), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated under reduced pressure and the residue was subjected to azeotropic evaporation with toluene (5 ml×2). The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-0:1) to give methyl 4-(2-acetoxyethyl)-6-cyclohexyl-5-(2,4-dihydroxyphenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate (762 mg, yield 94%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was subjected to azeotropic evaporation with toluene (5 ml×2)
  3. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-0:1)

Sources & evidence

ORD record
ord-dcc94d6711d14530bf39c60320144fa1
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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