Dibromomaleimide → Di-dansyl-cystamine maleimide

HRID 929391Notes

Reaction equation

HRID 929391 reaction equation
[S:1]([N:17]([S:25]([C:28]1[C:40]2[CH:39]=[CH:38][CH:37]=[C:33]([N:34]([CH3:36])[CH3:35])[C:32]=2[CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH2:18][CH2:19][S:20][S:21][CH2:22][CH2:23][NH2:24])([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2].C(C(O)=O)CP(CCC(O)=O)CCC(O)=O.Br[C:58]1[C:63](=[O:64])[NH:62][C:60](=[O:61])[C:59]=1Br.CC([O-])=O.[Na+]>CO>[S:1]([N:17]([S:25]([C:28]1[C:40]2[CH:39]=[CH:38][CH:37]=[C:33]([N:34]([CH3:36])[CH3:35])[C:32]=2[CH:31]=[CH:30][CH:29]=1)(=[O:26])=[O:27])[CH2:18][CH2:19][S:20][S:21][CH2:22][CH2:23][NH2:24])([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:11])[CH3:12])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2].[C:60]1(=[O:61])[NH:62][C:63](=[O:64])[CH:58]=[CH:59]1

Participants

6

Reactant 4

HCID 14279DibromomaleimideHCID 119411Tris(2-carboxyethyl)phosphineHCID 517045Sodium AcetateHCID 86668292Di-dansyl cystamine

Product 1

HCID 86668291Di-dansyl-cystamine maleimideYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A round bottomed flask was charged with di-dansyl cystamine (100 mg, 0.16 mmol), TCEP (46 mg, 1 eq) and MeOH (10 ml). The reaction mixture was stirred at ambient temperature under argon for 3 hrs. Dibromomaleimide (36 mg, 0.9 eq), in MeOH (5 ml) was then added to the reaction mixture. After 30 mins NaOAc (56 mg, 4 eq), was added to the reaction mixture and the solvent evaporated in vacuo. The residue was worked up with DCM and brine. The organic layers were combined, dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, 0-20% EtOAc-DCM) afforded the desired compound as a yellow gum (40 mg, 40%). 1HNMR (CDCl3, 600 MHz), δ8.5 (2H, d J 8.5 Hz aromatic H's), δ8.2 (4H, m aromatic H's), δ7.53 (1H, s CONH), δ7.46 (4H, m, aromatic H's), δ7.1 (2H, d, J=7.4 Hz aromatic H's), δ5.65 (2H, t, J 6.27 SO2NH), δ3.3 (4H, t, J 6.0 SCH2), δ3.17 (4H, q, J 6.0 NHCH2), δ2.8 (12H, s NCH3); 13CNMR (CDCl3, 150 MHz), 6165.9, 152.0, 136.5, 134.7, 130.7, 129.94, 129.85, 129.62, 129.57, 128.63, 123.3, 118.8, 115.4, 45.5, 43.6, 31.8; IR (cm−1) 3288 (br) 1720 (s) MS (Na+) m/z relative intensity: 736 (M, 100); Exact mass calculated for [C32H35N5O6NaS4] requires m/z 736.1368. Found 736.1390 (Na+).

Workup

  1. additionwas added to the reaction mixture
  2. customthe solvent evaporated in vacuo
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (silica gel, 0-20% EtOAc-DCM)

Sources & evidence

ORD record
ord-81423163d5da4e28a6048f46f2c7e8e4
Source dataset
uspto-grants-2016_03
Patent number
US09295729B2

Reaction notes

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