1,2-Dimethylindole-3-sulfonyl (MIS) as protecting group for the side chain of arginine

Organic and Biomolecular Chemistry

Volumn 7, Issue 12, 2009, Pages 2565-2569

  Isidro, Albert ^a   Latassa, Daniel ^b   Giraud, Matthieu ^b   Álvarez, Mercedes ^a,c   Albericio, Fernando ^a,c  

^a INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^b LONZA AG   (Switzerland)

^c UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACID STABILITY; ACID-LABILE; GUANIDINIUM; LARGE SCALE SYNTHESIS; PEPTIDE CHEMISTRIES; PROTECTING GROUP; SIDE CHAINS; SIDE REACTIONS;

ACIDS; AMINES; PEPTIDES; SWITCHING CIRCUITS;

AMINO ACIDS;

1,2 DIMETHYLINDOLE 3 SULFONYL CHLORIDE; 1,2-DIMETHYLINDOLE-3-SULFONYL CHLORIDE; ARGININE; BENZOFURAN DERIVATIVE; INDOLE DERIVATIVE; PEPTIDE; SCAVENGER; SULFINIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; PH; SYNTHESIS;

ARGININE; BENZOFURANS; FREE RADICAL SCAVENGERS; HYDROGEN-ION CONCENTRATION; INDOLES; PEPTIDES; SULFINIC ACIDS;

EID: 67650447050     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b904836g     Document Type: Article

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26. 2O was added (400 mL). The resulting solution was washed with diethyl ether (4 × 250 mL). The aqueous phase was evaporated to dryness and dried in the vacuum dessicator to render a red oily solid (96% yield), which was characterized by NMR and HRMS.
27. 2O (100 mL) was added, the pH was adjusted firstly to 10 and finally to 3.0. At this point, the aqueous phase was discharged. This process was repeated and the EtOAc solution was concentrated to give a light yellow solid (2.9 g, yield: 24.5%, HPLC purity: 70.6%).