Triethylamine → HCID 56610267, compound

HRID 1421846Notes

Reaction equation

HRID 1421846 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-b40c75b295ef40d48e746500c59f8903
Source dataset
uspto-grants-2000_06
Patent number
US06080591

Reaction notes

Loading…