Tris(2-carboxyethyl)phosphine → HCID 86668295, compound

HRID 929393Notes

Reaction equation

HRID 929393 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[C:58]1[C:59]([NH:61][C:62](=[O:64])[CH:63]=1)=[O:60]>CO>[S:1]([NH:17][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:2])=[O:3].[C:59]1(=[O:60])[NH:61][C:62](=[O:64])[CH:63]=[CH:58]1

Participants

5

Reactant 3

HCID 119411Tris(2-carboxyethyl)phosphineHCID 118195503-bromo-2,5-dihydro-1H-pyrrole-2,5-dioneHCID 86668292Di-dansyl cystamine

Product 1

HCID 86668295HCID 86668295, compoundYield 94.5%

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. Bromomaleimide (56 mg, 2 eq) in MeOH (5 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, 0-30% EtOAC-CHCl3) to yield the desired compound (73 mg, 55%). 1HNMR (CDCl3, 600 MHz), δ8.5 (1H, d J 8.5 Hz aromatic H's), δ8.2 (2H, m aromatic H's), δ8.1 (1H, s CONH), δ7.5 (2H, m, aromatic H's), δ7.15 (1H, d, J=7.5 Hz aromatic H's), δ6.0 (1H, s, CO2CH) δ5.89 (1H, t, J 6.4 SO2NH), δ3.20 (2H, q, J 6.7 NHCH2), δ3.99 (2H, t, J 6.9 SCH2), δ2.86 (6H, s NCH3); 13CNMR (CDCl3, 150 MHz), 6169.6, 168.0, 152.0, 150.7, 134.4, 131.0, 129.9, 129.7, 129.5, 128.8, 123.4, 119.3, 118.7, 115.6, 45.5, 41.0, 31.8; IR (cm−1) 3277 (br) 1720 (s) MS (ES−) m/z relative intensity: 404 (M, 100); Exact mass calculated for [C18H18N3O4S2] requires m/z 404.0739. Found 404.0733.

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, 0-30% EtOAC-CHCl3)

Sources & evidence

ORD record
ord-63ad4eb0dde2472c9ae062712402014f
Source dataset
uspto-grants-2016_03
Patent number
US09295729B2

Reaction notes

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