A convergent synthesis of poststatin: Application of the acyl cyanophosphorane coupling procedure in the formation of a peptidic α-keto amide

Tetrahedron Letters

Volumn 38, Issue 6, 1997, Pages 953-956

  Wasserman, Harry H ^a   Petersen, Anders K ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; PENTAPEPTIDE; POSTATIN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031562065     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02488-4     Document Type: Article

References (45)

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36. 13C NMR, MS, and HRMS.
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40. 21 (Cyanomethyl)triphenylphosphonium chloride (Lancaster Synthesis Inc.) (123.6 g, 0.37 mol) was suspended in dry dichloromethane (1.8 L). Triethylamine (127 mL, 92.2 g, 0.91 mol) was added over a period of 15 min. The clear yellow solution was stirred for a further 25 min, before it was washed with prechilled water (2 × 500 mL) and dried with magnesium sulfate (1 h). Filtration and concentration afforded a pale yellow solid (108.1 g, 0.36 mol, 98% yield). The crude ylide was contaminated with less than 5% triphenylphosphine oxide and could be condensed successfully with carboxylic acids. The product was purified by recrystallization from benzene (1.5 L, 14 mL/g) to give an off-white product (87.0 g, 0.29 mol, 79%).
41. 23. Along with amine 9 (53%), the cyclic amidine 9a (21%) formed by intramolecular aminolysis of the cyano group (26% unconverted 8). (equation presented)
42. 24. Prepared from valylvaline (85%) by reaction with benzyl chloroformate.
43. 1d,f by treatment with saturated aqueous sodium hydrogen carbonate.
44. 1d,f was obtained in impure state after chromatography. At 0.1 mmol scale the yield was consistently in the 50% range, and the product quality was significantly higher.
45. 13C NMR spectra, the final comparison was achieved by mixing equal amounts of the two samples. Under these circumstances, a single set of signals was observed.