Cesium carbonate → Racemic benzyl 1-(3-bromo-2-methylphenyl)-2-oxopyrrolidin-3-ylcarbamate

HRID 1811082Notes

Reaction equation

HRID 1811082 reaction equation
[I-].[CH2:2]([O:9][C:10]([NH:12][CH:13]([C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[C:23]=1[CH3:29])=[O:20])[CH2:14][CH2:15][S+](C)C)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.CCOC(C)=O>[Br:28][C:24]1[C:23]([CH3:29])=[C:22]([N:21]2[CH2:15][CH2:14][CH:13]([NH:12][C:10](=[O:11])[O:9][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:19]2=[O:20])[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 87071307Racemic (3-(benzyloxycarbonylamino)-4-(3-bromo-2-methylphenylamino)-4-oxobutyl)dimethylsulfonium iodide

Product 1

HCID 59375064Racemic benzyl 1-(3-bromo-2-methylphenyl)-2-oxopyrrolidin-3-ylcarbamateYield 94%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Step 3 A solution of racemic (3-(benzyloxycarbonylamino)-4-(3-bromo-2-methylphenylamino)-4-oxobutyl)dimethylsulfonium iodide (1.96 g, 3.30 mmol) in anhydrous DMSO (33 mL) was stirred at rt and treated with cesium carbonate (2.69 g, 8.26 mmol) in 3 portions over 25 min. After 4.5 h, the mixture was diluted with EtOAc, washed three times with water and twice with brine, dried and concentrated to provide racemic benzyl 1-(3-bromo-2-methylphenyl)-2-oxopyrrolidin-3-ylcarbamate as a tan solid (1.248 g, 94%). 1H NMR (400 MHz, chloroform-d) δ 7.52-7.58 (1H, m), 7.30-7.40 (5H, m), 7.10 (2H, d, J=5.1 Hz), 5.47 (1H, br. s.), 5.15 (2H, s), 4.39 (1H, ddd, J=10.6, 8.3, 5.2 Hz), 3.72 (1H, td, J=9.9, 6.4 Hz), 3.60 (1H, t, J=9.4 Hz), 2.27 (3H, s), 2.11-2.26 (2H, m). Mass spectrum m/z 425, 427 (M+Na)+.

Workup

  1. washwashed three times with water
  2. dry with materialtwice with brine, dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-37206c5e7199455ba49a96279df1277a
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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