HCID 70615964, compound → HCID 131710420, compound

HRID 1282993Notes

Reaction equation

HRID 1282993 reaction equation
[O:1]([CH2:8][C:9]([NH:11][C@@H:12]1[C:28](=[O:29])[N:14]2[C:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:16]([CH:19]=[CH2:20])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C>[CH2:19]([C:16]1[CH2:17][S:18][C@@H:13]2[C@H:12]([NH:11][C:9](=[O:10])[CH2:8][O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:28](=[O:29])[N:14]2[C:15]=1[C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[CH3:20]

Participants

4

Reactant 2

HCID 70615964HCID 70615964, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131710420HCID 131710420, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Hydrogen was bubbled through a suspension of 10%-palladium on carbon (3 g, 0.00282 g atoms) in dry ethyl acetate (100 ml.) for 30 minutes. A solution of t-butyl 7β-phenoxyacetamido-3-vinylceph-3-em-4-carboxylate (1.4 g., 3.36 mmole) in dry ethyl acetate (50 ml.) was added and the mixture was stirred for 21/2 hours in a hydrogen stream and filtered through a bed of kieselguhr. The filtrate was evaporated in vacuo to give the title ester as a white foam (1.21 g, 86.5%), [α]D23 + 55.4° (c 0.85; CHCl3), λmax. (EtOH) 263 nm(ε 8,100) and 268 nm (ε 8,450), inflexion at 273 nm (ε 7,600), νmax. (CHBr3) 3420(NH), 1782 (azetidin-2-one), 1715 (CO2R), and 1695 and 1525 cm.-1 (CONH), τ (CDCl3) 2.66 and 3.03 (2H and 3H, two m; C6H5O) 4.15 (1H, dd, J 9.5 and 5 Hz; C7 --H), 5.00 (1H, d, J 5 Hz; C6 --H) 5.45 (2H, s; C6H5OCH2), 6.51 and 6.73 (2H, AB-q, J 18 Hz; C2 --H2), 7.37 and 7.80 (2H, AB-part of ABX3 -system, JAX, JBX 7 Hz, JAB 13 Hz; C3 --CH2CH3), 8.47 (9 H, s; CO2C(CH3)3), 8.87 (3 H, t, J 7 Hz; CH2CH3) (Found: C, 60.1; H, 6.3; N, 6.7; S, 7.2. C21H26N2O5S (418.5) requires C, 60.25; H, 6.2; N, 6.8; S, 7.7%).

Workup

  1. customHydrogen was bubbled through a suspension of 10%-palladium on carbon (3 g, 0.00282 g atoms) in dry ethyl acetate (100 ml.) for 30 minutes
  2. filtrationfiltered through a bed of kieselguhr
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-cba1a9a168e84911a0b8d92168d3c23e
Source dataset
uspto-grants-1976_08
Patent number
US03974152

Reaction notes

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