Triethylamine → 4-[3-(4-Nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one

HRID 435089Notes

Reaction equation

HRID 435089 reaction equation
C(N(CC)CC)C.O[C@@H]([C@@H:11]1[C@@H:14]([CH2:15][C:16](=[O:31])[CH2:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])[NH:13][C:12]1=[O:32])C.C(C1C=CC(S([N:45]=[N+:46]=[N-])(=O)=O)=CC=1)(O)=O>C(#N)C>[N+:28]([C:25]1[CH:26]=[CH:27][C:22]([CH2:21][O:20][C:18]([C:17](=[N+:45]=[N-:46])[C:16](=[O:31])[CH2:15][CH:14]2[NH:13][C:12](=[O:32])[CH2:11]2)=[O:19])=[CH:23][CH:24]=1)([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 86999Benzoic acid, 4-(azidosulfonyl)-HCID 13018177(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxopropyl]azetidin-2-one

Product 1

HCID 539743044-[3-(4-Nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylamine (263 mg, 2.6 mmol) is added by syringe to a mixture of (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxopropyl]azetidin-2-one, (253 mg, 0.72 mmol) and p-carboxybenzene sulfonylazide (196 mg, 0.84 mmol) in dry acetonitrile (6 ml) at 0° C. When addition is complete the cooling bath is removed and the reaction mixture is stirred at room temperature for 1 hour. The mixture is then diluted with ethyl acetate (50 ml) and filtered. The filtrate is concentrated in vacuo and the residue is chromatographed on a short silica gel column (ethyl acetate) to yield 222 mg, (81% overall from (3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxopropyl]azetidin-2-one) of (3S,4R)-3-(R)-1-hydroxyethyl)-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one as a white solid m.p. (dec.) 163° C. IR(CHCl3, CM-1) 3410, 2132, 1756, 1718, 1650, 1350, 1280, 1120; n.m.r. (CDCl3) δ7.9 (2d-aromatic,4), δ5.4 (s,2), δ6.2 (brs,1), δ4.1 (m,2), δ2.6-3.6 (m,4), δ1.32 (d,3,J=6.2).

Workup

  1. additionWhen addition
  2. customis removed
  3. additionThe mixture is then diluted with ethyl acetate (50 ml)
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in vacuo
  6. customthe residue is chromatographed on a short silica gel column (ethyl acetate)

Sources & evidence

ORD record
ord-87b3bd1037464b77ae6a677280e3238c
Source dataset
uspto-grants-1983_08
Patent number
US04400323

Reaction notes

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