Pyridine → N-[4-(5-carboxypentylcarbamoyl)-cyclohexylmethyl]-2-(carboxy)ethyl thiosuccinimide

HRID 260222

Reaction equation

HRID 260222 reaction equation
[CH2:1]1[CH:6]([CH2:7][N:8]2[C:13](=O)[CH:12]=[CH:11][C:9]2=[O:10])[CH2:5][CH2:4][CH:3]([C:15]([O:17]N2C(=O)CCC2=O)=O)[CH2:2]1.[C:25]([O-:32])(=[O:31])[CH2:26][CH2:27]CCC.[CH2:33]([C:36]([OH:38])=[O:37])[CH2:34]S.C1C([S:45]SC2C=CC([N+]([O-])=O)=C(C(O)=O)C=2)=CC(C(O)=O)=C([N+]([O-])=O)C=1.[N:65]1C=C[CH:68]=[CH:67][CH:66]=1>>[C:36]([CH2:33][CH2:34][CH2:68][CH2:67][CH2:66][NH:65][C:15]([CH:3]1[CH2:2][CH2:1][CH:6]([CH2:7][N:8]2[C:9](=[O:10])[CH2:11][CH:12]([CH2:27][CH2:26][C:25]([OH:32])=[O:31])[C:13]2=[S:45])[CH2:5][CH2:4]1)=[O:17])([OH:38])=[O:37]

Participants

5

Reactant 4

HCID 1049PyridineHCID 62545,5'-Dithiobis(2-nitrobenzoic Acid)HCID 65143-Mercaptopropionic AcidHCID 131719433SMCC caproate

Product 1

HCID 86749545N-[4-(5-carboxypentylcarbamoyl)-cyclohexylmethyl]-2-(carboxy)ethyl thiosuccinimide

Procedure

SMCC-caproate (0.01 g, 2.86×10-5 mol) was dissolved in 0.071 ml pyridine and 0.016 ml (6.4×10-6 mol) of the solution aliquoted into a test tube. Mercaptopropionic acid (0.0056 ml of 1.15M solution in dimethylformamide, 6.4×10-6 mol) was added to the tube, the solution gassed with argon, and the tube sealed. After 12 hr at room temperature, no thiol remained (as determined by reaction with DTNB) and the solvents were removed in vacuo. The residue was dissolved in 0.03 ml of 0.2M potassium phosphate, pH 7, to make a 213 mM solution of the desired compound (see FIG. 1D).

Workup

  1. customthe tube sealed
  2. customthe solvents were removed in vacuo
  3. dissolutionThe residue was dissolved in 0.03 ml of 0.2M potassium phosphate

Sources & evidence

ORD record
ord-f7ba4cf8a08b4a57a77587bc810e9448
Source dataset
uspto-grants-1996_06
Patent number
US05525524

Linked notes

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