Hydrochloric Acid → HCID 88794739, compound

HRID 1390412Notes

Reaction equation

HRID 1390412 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:28])[C:19]([C:23]3[O:24][CH:25]=[CH:26][CH:27]=3)=[N:20][O:21][CH3:22])[C:15](=[O:29])[N:10]2[C:11]=1[C:12]([O-:14])=[O:13])(=[O:3])[NH2:2].[Na+].[Na].Cl.[OH2:33]>>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S@:8](=[O:33])[C@@H:9]2[C@H:16]([NH:17][C:18](=[O:28])[C:19]([C:23]3[O:24][CH:25]=[CH:26][CH:27]=3)=[N:20][O:21][CH3:22])[C:15](=[O:29])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[NH2:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5360545SodiumHCID 23667302HCID 23667302, compound

Product 1

HCID 88794739HCID 88794739, compound

Procedure

To a stirred solution of sodium (6R,7R)-3-carbamoyloxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylate (syn isomer) (2.59 g) in water (25 ml) was added sodium metaperidoate (1.93 g). The solution was stirred for 30 minutes at ambient temperature and then acidified by the dropwise addition of 2N aqueous hydrochloric acid. The resulting precipitate was collected, washed successively with water, ethanol and ether and then dried in vacuo to afford the title compound as a white powder (1.63 g.), [α]D20 + 113° (c 0.86, Me2SO); λmax (pH6 buffer) 264.5 (ε 17,200) and 279 nm (ε 15,600); νmax (Nujol) 1779 (β-lactam), 1740 and 1716(CO2H), 1688, 1654, 1589 and 1530 (CONH and OCONH2) and 1030cm-1 (S→O), τ (Me2SO-d6)0.60 (d, J 8Hz, NH), 2.11, 3.19, 3.31 (multiplets, furyl protons), 4.08 (q, J5 and 8Hz, C-7H). 4.87 and 5.45 (ABq, J13Hz, CH2OCONH2), 4.96(d, J 5Hz, C-6H), 6.08 (s, OCH3), 6.10 and 6.42(ABq, J 18Hz, C-2 CH2).

Workup

  1. customThe resulting precipitate was collected
  2. washwashed successively with water, ethanol and ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-0453b522155846aeab8d6e8e981ebe0d
Source dataset
uspto-grants-1979_02
Patent number
US04138555

Reaction notes

Loading…