N-bromobutanimide → methyl 4-[(1S)-1-({[5-bromo-4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoate

HRID 870043Notes

Reaction equation

HRID 870043 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:11]=[C:12]([CH:34]=[CH:35][CH:36]=1)[CH2:13][C:14]1[C:15]([C:19]([NH:21][C@H:22]([C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=2)[CH3:23])=[O:20])=[CH:16][S:17][CH:18]=1.C(Cl)Cl.CC(O)=O>C([O-])(O)=O.[Na+]>[Br:1][C:18]1[S:17][CH:16]=[C:15]([C:19]([NH:21][C@H:22]([C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=2)[CH3:23])=[O:20])[C:14]=1[CH2:13][C:12]1[CH:34]=[CH:35][CH:36]=[C:10]([Cl:9])[CH:11]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 21922555Acetic acid methylene chlorideHCID 45140964methyl 4-[(1S)-1-({[4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoate

Product 1

HCID 57900972methyl 4-[(1S)-1-({[5-bromo-4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoate

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

N-Bromosuccinimide (43.0 mg, 0.242 mmol) was added to methyl 4-[(1S)-1-({[4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoate from Example 3, Step 4 (50.0 mg, 0.121 mmol) in 1:1 CH2Cl2/AcOH (1.2 mL). After 16 h, the reaction was slowly poured in 5% aq. NaHCO3. The aqueous layer was extracted with CHCl3 and the combined organics were washed with 5% aq. NaHCO3, sat. Na2S2O3 and brine, dried (Na2SO4) and concentrated. The crude product was purified by Combi Flash chromatography system (0-2% EtOAc/CHCl3 in 15 min.) to afford the desired product as a brown solid.

Workup

  1. extractionThe aqueous layer was extracted with CHCl3
  2. washthe combined organics were washed with 5% aq. NaHCO3, sat. Na2S2O3 and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by Combi Flash chromatography system (0-2% EtOAc/CHCl3 in 15 min.)

Sources & evidence

ORD record
ord-6c5d3b979248441abf1f31fbd2891630
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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