4-Nitrobenzaldehyde → Benzyl 6beta-(4-nitrobenzylideneamino)penam-3-caboxylate

HRID 64763Notes

Reaction equation

HRID 64763 reaction equation
[NH2:1][C@@H:2]1[C:18](=[O:19])[N:4]2[CH:5]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:6][S:7][C@H:3]12.COC(OC)OC.[N+:27]([C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1)([O-:29])=[O:28]>ClCCl.CO>[N+:27]([C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[N:1][C@@H:2]2[C:18](=[O:19])[N:4]3[CH:5]([C:8]([O:10][CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[O:9])[CH2:6][S:7][C@H:3]23)=[CH:32][CH:31]=1)([O-:29])=[O:28]

Participants

6

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 9005Trimethyl orthoformateHCID 70378555HCID 70378555, compound

Product 1

HCID 13644184Benzyl 6beta-(4-nitrobenzylideneamino)penam-3-caboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Benzyl 6β-aminopenam-3-carboxylate (1.11 g, 4 m mol) in dry dichloromethane (4ml) with trimethylorthoformate (0.42 g, 0.44 ml, 4 m mol) was treated with 4-nitrobenzaldehyde (0.61 g, 0.4 m mol) in dry methanol (10 ml) at room temperature for 1.5 h. The mixture was then evaporated to dryness, triturated with ethanol and the solid material collected by filtration. Renystallisation from ethanol/ethylacetate gave almost colourless needles (1.2 g 74%); m.p. 95-96 C; νmax (CH2Cl2) 1795, 1750, 1530, 1360 cm-1 ; δ(CDCl3) 8.68 (1H, d, J 2Hz, CH=N), 8.27 and 7.94 (4H, 2d, J 9Hz, nitrophenyl), 7.38 (5H, s, phenyl), 5.51 (1H, d, J 4Hz, 5-H), 5.45 (1H, dd, J 2Hz and 4 Hz, 6-H), 5.23 (2H, s, CH2Ph), 4.93 (1H, t, J 5.5Hz, 3-H) and 3.45 (2H, d, J 5.5H±, 2-H)

Workup

  1. customThe mixture was then evaporated to dryness
  2. customtriturated with ethanol
  3. filtrationthe solid material collected by filtration
  4. customRenystallisation from ethanol/ethylacetate gave almost colourless needles (1.2 g 74%)

Sources & evidence

ORD record
ord-a5f7d684d7404733a8d26192b2d7931d
Source dataset
uspto-grants-1986_09
Patent number
US04609652

Reaction notes

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