1,4-Dioxane → HCID 70507138, compound

HRID 2296569Notes

Reaction equation

HRID 2296569 reaction equation
[OH:1][CH:2]1[C@@H:6]2[CH:7]([NH:10][C:11](=[O:32])[CH:12]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:13][C:14]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH3:23])[C:18](=[O:24])[C:17]3=[O:25])=[O:15])[C:8](=[O:9])[N:5]2[CH:4]([C:33]([O:35]CC2C=CC3C(=CC=CC=3)C=2)=[O:34])[CH:3]1[CH3:47].O1CCOCC1.C(=O)(O)[O-].[Na+:58]>[Pd].C(O)(=O)C.C(O)C.C(Cl)(Cl)Cl.O.CC(C)=O>[OH:1][CH:2]1[C@@H:6]2[CH:7]([NH:10][C:11](=[O:32])[CH:12]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[NH:13][C:14]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH3:23])[C:18](=[O:24])[C:17]3=[O:25])=[O:15])[C:8](=[O:9])[N:5]2[CH:4]([C:33]([O-:35])=[O:34])[CH:3]1[CH3:47].[Na+:58]

Participants

10

Reactant 3

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 70507910HCID 70507910, compound

Product 1

HCID 70507138HCID 70507138, compound

Reagents, catalysts & solvents 6

HCID 23938PalladiumCatalyst2×HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

2-Naphthylmethyl 1-hydroxy-2-methyl-6-[2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]carbapenam-3-carboxylate (36 mg., 0.056 mmole) was dissolved in 2 ml. of dioxane. Water (1 ml.), sodium bicarbonate (4.7 mg., 0.056 mmole) and hydrogenation catalyst (36 mg. of 10% palladium on carbon) were added and the mixture was hydrogenated at 50 psig and room temperature for 30 minutes. Monitoring by tlc (9:1 acetone:water and 90:10:2 chloroform:ethanol:acetic acid) indicated that hydrogenation was incomplete. An additional 36 mg. of 10% palladium on carbon was added and hydrogenation, under the same conditions, resumed for 30 minutes, at which time tlc monitoring indicated reaction was complete. Catalyst was recovered by filtration and the filtrate freeze dried to yield sodium 1-hydroxy-2-methyl-6-[2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]carbapenam-3-carboxylate [10 mg., 34%; Rf 0.3 (9:1 acetone:water; Rf 0.3 (90:10:2 chloroform:ethanol:acetic acid); ir (nujol mull) 1770, 1750, 1710 cm-1 ].

Workup

  1. waithydrogenation, under the same conditions, resumed for 30 minutes, at which time tlc monitoring
  2. customreaction
  3. filtrationCatalyst was recovered by filtration
  4. customthe filtrate freeze dried

Sources & evidence

ORD record
ord-4d35967da62a475ca79947fc9dbd9add
Source dataset
uspto-grants-1984_01
Patent number
US04429128

Reaction notes

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