Synthesis of (S,S)-3-prolylazetidin-2-one: A key component in the synthesis of an HIV gp120 constrained immunogen

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 965-968

  Qabar, Maher N ^a   Kahn, Michael ^a,b  

^a Molecumetics Ltd   (United States)

^b UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE; 3 PROLYL 2 AZETIDINONE; ANTIGEN; GLYCOPROTEIN GP 120; UNCLASSIFIED DRUG;

ARTICLE; DRUG DEVELOPMENT; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030062673     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02340-2     Document Type: Article

References (27)

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19. Flash chromatography afforded the (S,S) diastereomer (67%) in addition to an approximately 1:1 mixture of the (S,S) and (R,S) diastereomers (21%). The (R,S) diastereomer was obtained from the displacement of the (S)-bromohydroxamate (ent 7), which was formed during the bromination step.
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25. Prewash of the RaNi™ and duration of the reaction are necessary to eliminate rearrangement.
26. 3, 500 MHz): δ 1.94 (3H, m), 2.19 (1H, m), 2.80 (1H, dd, J = 17.0, 8.5 Hz), 3.20 (1H, m), 3.40 (1H, dd, J = 5.5, 2.5 Hz), 3.44 (1H, dd, J = 5.5, 5.5 Hz), 3.71 (3H, s), 3.81 (1H, dd, J = 8.5, 5.5 Hz), 4.45 (1H, ddd, J = 5.0, 2.5, 1.5 Hz), 5.68 (1H, br s).
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