Dibromomaleimide → Bromo-dansyl-cystamine maleimide

HRID 929392Notes

Reaction equation

HRID 929392 reaction equation
[S:1]([N:17](S(C1C2C=CC=C(N(C)C)C=2C=CC=1)(=O)=O)[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:57][C:58]1[C:63](=[O:64])[NH:62][C:60](=[O:61])[C:59]=1Br>CO>[Br:57][N:17]([S:1]([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])[CH2:18][CH2:19][S:20][S:21][CH2:22][CH2:23][NH2:24].[C:60]1(=[O:61])[NH:62][C:63](=[O:64])[CH:58]=[CH:59]1

Participants

5

Reactant 3

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

Product 1

HCID 86668293Bromo-dansyl-cystamine maleimideYield 37.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A round bottomed flask was charged with di-dansyl cystamine (48 mg, 0.08 mmol), TCEP (23 mg, 1 eq), and MeOH (10 ml). The reaction mixture was stirred at ambient temperature under argon for 3 hrs. Dibromomaleimide (41 mg, 2 eq) in MeOH (10 ml), was added to the reaction mixture. After 16 hrs, the reaction mixture was concentrated in vacuo. The residue was worked up with DCM and brine. The organic layers were combined, dried (MgSO4) and purified by flash chromatography (silica gel, 0-15% EtOAC-DCM) to yield the desired compound (17 mg, 22%). 1HNMR (CDCl3, 600 MHz), δ8.5 (1H, d J 8.5 Hz aromatic H's), δ8.2 (2H, m aromatic H's), δ7.6 (1H, s CONH), δ7.53 (2H, m, aromatic H's), δ7.15 (1H, d, J=7.4 Hz aromatic H's), δ5.30 (1H, t, J 5.6 SO2NH), δ3.38 (2H, t, J 6.3 SCH2), δ3.26 (2H, q, J 6.3 NHCH2), δ2.88 (6H, s NCH3); 13CNMR (CDCl3, 150 MHz), δ165.5, 162.9, 152.2, 142.5, 134.5, 130.95, 129.94, 129.92, 129.5, 128.7, 123.3, 119.0, 118.5, 115.4, 45.5, 43.7, 30.5; IR (cm−1) 3295 (br) 1726 (s) MS (ES+) m/z relative intensity: 485 (M, 100); Exact mass calculated for [C18H19N3O4S2Br] requires m/z 484.0000. Found 783.9982.

Workup

  1. waitAfter 16 hrs
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dry with materialdried (MgSO4)
  4. custompurified by flash chromatography (silica gel, 0-15% EtOAC-DCM)

Sources & evidence

ORD record
ord-cf62c96af71540898c93538e9df9446a
Source dataset
uspto-grants-2016_03
Patent number
US09295729B2

Reaction notes

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