Triethylamine → HCID 56610267, compound

HRID 1735683Notes

Reaction equation

HRID 1735683 reaction equation
[C:1]([O:5][C:6]([O:8]N=C(C1C=CC=CC=1)C#N)=O)([CH3:4])([CH3:3])[CH3:2].[S:19]([CH2:23][CH2:24][CH2:25][S:26][CH2:27][C@@H:28]([C:30]([OH:32])=[O:31])[NH2:29])([OH:22])(=[O:21])=[O:20].C(N(CC)CC)C.C(Cl)(Cl)Cl.CO.O>O1CCOCC1.O>[C:1]([O:5][C:6]([NH:29][C@H:28]([C:30]([OH:32])=[O:31])[CH2:27][S:26][CH2:25][CH2:24][CH2:23][S:19]([OH:22])(=[O:20])=[O:21])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 21866399Chloroform methanol waterHCID 53471022HCID 53471022, compound2×

Product 1

HCID 56610267HCID 56610267, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (BOC-ON) (121 mg, 0.49 mmole) (Aldrich Chem. Co., Milwaukee, Wis.) was added to a solution of S-(3-sulfopropyl)cysteine (SulfoCys, 100 mg, 0.41 mmole), (prepared by the method of U. T. Ruegg and J. Rudinger, J. Peptide Protein Res. 6, 447, 1974), and triethylamine (O.18 ml, 1.23 mmole) in 3 ml of 50% aqueous dioxane to form a reaction mixture. The reaction mixture was heated at 50°-55° C. for 1 hour to obtain a yellow solution. The reaction mixture was then cooled, diluted with 5 ml of water, and washed with ethylacetate (3×10 ml). The resultant aqueous layer was evaporated to dryness under vacuo by coevaporating with methanol twice. TLC (Silica gel 60, Merck & Co., Inc.) analysis of the residue produced by the evaporation, using a solvent system of chloroform/methanol/water (55:40:5), showed complete conversion of SulfoCys to BOC-SulfoCys.

Workup

  1. custom(prepared by the method of U
  2. temperatureThe reaction mixture was heated at 50°-55° C. for 1 hour
  3. customto obtain a yellow solution
  4. temperatureThe reaction mixture was then cooled
  5. washwashed with ethylacetate (3×10 ml)
  6. customThe resultant aqueous layer was evaporated to dryness under vacuo
  7. customTLC (Silica gel 60, Merck & Co., Inc.) analysis of the residue produced by the evaporation

Sources & evidence

ORD record
ord-91f2d2e2213b415f8a39edc26ce2bda1
Source dataset
uspto-grants-1996_07
Patent number
US05538901

Reaction notes

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