Using mixed anhydrides from amino acids and isobutyl chloroformate in N-acylations: A case study on the elucidation of mechanism of urethane formation and starting amino acid liberation using carbon dioxide as the probe

Tetrahedron Letters

Volumn 44, Issue 29, 2003, Pages 5543-5546

  Chaudhary, Apurva ^a   Girgis, Michael ^a   Prashad, Mahavir ^a   Hu, Bin ^a   Har, Denis ^a   Repič, Oljan ^a   Blacklock, Thomas J ^a  

^a NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; AMINO ACID DERIVATIVE; CARBON DIOXIDE; CARBOXYLIC ACID; CHLORINE DERIVATIVE; ISOBUTYLCHLOROFORMATE; UNCLASSIFIED DRUG; URETHAN;

ACYLATION; ARTICLE; CASE STUDY; CHEMICAL STRUCTURE;

EID: 0037525384     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01329-7     Document Type: Article

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21. 4 (125.0 mL) and stirred for 10 min. The organic layer was separated and washed sequentially with water (125.0 mL), 5% aqueous sodium bicarbonate (125.0 mL), and water (125.0 mL). The organic layer was concentrated at a jacket temperature of 65±5°C in vacuo (150 mbar) to collect 340 mL (∼309.0 g) of solvent and obtain a of solution of BOC-(S)-3-(2-naphthyl)alanyl-N-benzyl-N-methylamide in toluene (2, 310.0 mL, 272.0 g; containing 68.0 g of 2, assumed 100% yield) that was used crude in the next step.