Tetrahydrofuran → HCID 13649061, compound

HRID 1982111Notes

Reaction equation

HRID 1982111 reaction equation
[NH2:1][C@H:2]([C:6]([NH:8][CH:9]([C:13]([O-:15])=[O:14])[C:10]([O-:12])=[O:11])=[O:7])[C@@H:3]([CH3:5])O.[CH3:16][CH:17](OC(/N=N/C(OC(C)C)=O)=O)C.[CH2:30]1COC[CH2:31]1>>[CH2:16]([O:15][C:13]([CH:9]([C:10]([O:12][CH2:30][CH3:31])=[O:11])[N:8]1[CH:3]([CH3:5])[CH:2]([NH2:1])[C:6]1=[O:7])=[O:14])[CH3:17]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 5363146Diisopropyl azodicarboxylateHCID 86740847HCID 86740847, compound

Product 1

HCID 13649061HCID 13649061, compound

Procedure

Ox-L-Threonylaminomalonate (0.45 g, 0.92 mmoles) and TPP (0.26 g, 0.1 mmoles) were dissolved in THF (15 mL). DIAD (0.196 mL, 0.1 mmoles) in THF (15 mL) was added dropwise over 0.5 hour, after which the reaction mixture was evaporated and chromatographed (silica, 9:1 methylene chloride to ether). A mixture (0.32 g) containing the product was eluted. By NMR this mixture contained the desired β-lactam along with the dehydropeptide and the pyrrolidinone. The ratio of products (73%) was roughly 2:1:1. Careful rechromatography (slower gradient) led to the isolation of the β-lactam 50 mg (0.1 mmoles, 11%); M.P. 140°-142° C. NMR (DCCl3): 1.16-1.14 (9H, m); 4.09-4.5 (7H, m); 5.13 (1H, s); 7.23 (5H, s); 7.3-7.66 (5H, m).

Workup

  1. customafter which the reaction mixture was evaporated
  2. customchromatographed (silica, 9:1 methylene chloride to ether)
  3. additionA mixture (0.32 g) containing the product
  4. washwas eluted

Sources & evidence

ORD record
ord-2f26e86ecc134491b678515c12a53fff
Source dataset
uspto-grants-1986_06
Patent number
US04595532

Reaction notes

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