Triethylamine → HCID 56610267, compound

HRID 1376314Notes

Reaction equation

HRID 1376314 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 (0.18 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-43b719e63cf1447381196a0bad0e0dc7
Source dataset
uspto-grants-1997_09
Patent number
US05663074

Reaction notes

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