Dibromomaleimide → Di-dansyl-cystamine maleimide

HRID 929391ノート

反応式

HRID 929391 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 86668291Di-dansyl-cystamine maleimide収率 40%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-81423163d5da4e28a6048f46f2c7e8e4
出典データセット
uspto-grants-2016_03
特許番号
US09295729B2

反応ノート

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