Diethyl Ether → HCID 57240513, compound

HRID 2419870Notes

Reaction equation

HRID 2419870 reaction equation
[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCOCC.[CH:21]([NH:23][C@@H:24]1[C:35](=[O:36])[N:26]2[C:27]([C:32]([OH:34])=[O:33])=[C:28]([CH3:31])[CH2:29][S:30][C@H:25]12)=[O:22]>O1CCCC1>[CH:21]([NH:23][C@@H:24]1[C:35](=[O:36])[N:26]2[C:27]([C:32]([O:34][CH:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:33])=[C:28]([CH3:31])[CH2:29][S:30][C@H:25]12)=[O:22]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 13104785HCID 13104785, compound

Product 1

HCID 57240513HCID 57240513, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of diphenyldiazomethane in ether (prepared from benzophenone hydrazone [21 g, 41.8 mmole]) was added to a solution of 7β-formamido-3-methylceph-3-em-4-carboxylic acid (9.7 g, 40.2 mmole) in tetrahydrofuran (150 ml) and the mixture was stirred overnight in the absence of light. The solvents were removed in vacuo and the residual oil was dissolved in methylene chloride (200 ml). The solution was washed with 3%-sodium hydrogen carbonate solution (2 × 100 ml), dried, and evaporated to a yellow oil which was triturated with ethyl acetate-ether to give the title ester as a white crystalline solid (8.15 g, 49.5%), m.p. 136° to 140°, [α]D23 + 38° (c 0.94; Me2SO), λmax. (EtOH) 258 nm (ε 6,800), νmax. (Nujol) 3330 (NH), 1771 (azetidin-2-one), 1707 (CO2R) and 1655 and 1523 cm-1 (CONH), τ (Me2SO-d6) 1.91 (1H, d, J 9.5 Hz; NH), 1.89 (1H, s; CHO), 2.4 to 2.8 (10H, m; (C6H5)2CH), 3.07 (1H, s; (C6H5)2CH), 3.19 (1H,dd, J 9.5 and 5 Hz; C7 --H), 4.83 (1H,d, 5 Hz; C6 --H), 6.33 and 6.57 (2H, AB-q, 18 Hz; C2 --H2), 7.95 (3H, S; C3 --CH2) (Found: C, 64.55; H, 4.9; N, 6.7; S, 7.7. C22H20N2O4S (408.5) requires C, 64.7; H, 4.9; N, 6.9; S, 7.85%).

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residual oil was dissolved in methylene chloride (200 ml)
  3. washThe solution was washed with 3%-sodium hydrogen carbonate solution (2 × 100 ml)
  4. customdried
  5. customevaporated to a yellow oil which
  6. customwas triturated with ethyl acetate-ether

Sources & evidence

ORD record
ord-fc5d107537154fc09e709b1cd29cbf8f
Source dataset
uspto-grants-1978_08
Patent number
US04107431

Reaction notes

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