Dibromomaleimide → Di-dansyl-cystamine maleimide

HRID 929391노트

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HRID 929391 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 86668291Di-dansyl-cystamine maleimide수율 40%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-81423163d5da4e28a6048f46f2c7e8e4
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09295729B2

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