Triethylamine → HCID 86741284, compound

HRID 235759Notes

Reaction equation

HRID 235759 reaction equation
C1(C)C=CC(S([N:10]=[N+:11]=[N-])(=O)=O)=CC=1.[CH3:14][O:15][C:16]([C@@H:19]1[C:22](=[O:23])[NH:21][C@@H:20]1[CH2:24][C:25](=[O:40])[CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=1)=[O:28])([CH3:18])[CH3:17].C(N(CC)CC)C>C(#N)C>[N+:10](=[C:26]([C:25](=[O:40])[CH2:24][C@@H:20]1[C@H:19]([C:16]([O:15][CH3:14])([CH3:18])[CH3:17])[C:22](=[O:23])[NH:21]1)[C:27]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=1)=[O:28])=[N-:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 54000001HCID 54000001, compound

Product 1

HCID 86741284HCID 86741284, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of p-toluenesulfonyl azide (470 mg) in acetonitrile (4.23 ml) was added to a solution of 4-nitrobenzyl 4-[(2R,3R)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]-3-oxobutanoate (752 mg) in acetonitrile (15.04 ml) at 0° C. After stirring at 0° C. for 10 minutes, a solution of triethylamine (0.997 ml) in acetonitrile (8.973 ml) was added dropwise thereto. After stirring at 0° C. for an additional 50 minutes, the reaction mixture was evaporated. The residue was chromatographed on silica gel (11 g) eluting with 0-50% ethyl acetate in methylene chloride to give 4-nitrobenzyl 2-diazo-4-[(2R,3R)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]-3-oxobutanoate (733 mg).

Workup

  1. stirringAfter stirring at 0° C. for an additional 50 minutes
  2. customthe reaction mixture was evaporated
  3. customThe residue was chromatographed on silica gel (11 g)
  4. washeluting with 0-50% ethyl acetate in methylene chloride

Sources & evidence

ORD record
ord-8d318d8769b541b18a8e4abaebbac34c
Source dataset
uspto-grants-1987_02
Patent number
US04640915

Reaction notes

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