Mops → 2-(4-Methyl-1,2,3-triazol-1-yl)-carbapen-2-em-3-carboxylic acid

HRID 329671

Reaction equation

HRID 329671 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][N:5]([C:7]2[CH2:8][C@@H:9]3[CH2:26][C:25](=[O:27])[N:10]3[C:11]=2[C:12]([O:14]CC2C=CC([N+]([O-])=O)=CC=2)=[O:13])[CH:6]=1.[CH3:28][C:29]1[N:33]([C:34]2[CH2:35][C@@H:36]3[CH2:53][C:52](=[O:54])[N:37]3[C:38]=2[C:39]([O:41]CC2C=CC([N+]([O-])=O)=CC=2)=[O:40])[N:32]=[N:31][CH:30]=1.N1(CCCS(O)(=O)=O)CCOCC1>O1CCOCC1.O.C(O)C.[Pd]>[CH3:1][C:2]1[N:3]=[N:4][N:5]([C:7]2[CH2:8][C@@H:9]3[CH2:26][C:25](=[O:27])[N:10]3[C:11]=2[C:12]([OH:14])=[O:13])[CH:6]=1.[CH3:28][C:29]1[N:33]([C:34]2[CH2:35][C@@H:36]3[CH2:53][C:52](=[O:54])[N:37]3[C:38]=2[C:39]([OH:41])=[O:40])[N:32]=[N:31][CH:30]=1

Participants

9

Reactant 3

HCID 70807MopsHCID 131715753p-Nitrobenzyl 2-(4-methyl-1,2,3-triazol-1-yl)-carbapen-2-em-3-carboxylateHCID 131715754p-Nitrobenzyl 2-(5-methyl-1,2,3-triazol-1-yl)-carbapen-2-em-3-carboxylate

Product 2

HCID 1317157512-(4-Methyl-1,2,3-triazol-1-yl)-carbapen-2-em-3-carboxylic acidHCID 1317157522-(5-Methyl-1,2,3-triazol-1-yl)-carbapen-2-em-3-carboxylic acid

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of a mixture of p-nitrobenzyl 2-(4-methyl-1,2,3-triazol-1-yl)-carbapen-2-em-3-carboxylate and p-nitrobenzyl 2-(5-methyl-1,2,3-triazol-1-yl)-carbapen-2-em-3-carboxylate (0.7 mg) in dioxane (100 microliter), deionized water (60 microliter), absolute ethanol (8.3 microliter), and pH 7.0 0.5M aqueous 4-morpholinepropanesulfonic acid (10.2 microliter) was shaken with 10% (w/w) palladium on charcoal (1.0 mg) under hydrogen (50 psig) at ambient temperature. After 30 min. the mixture was centrifuged and the pellet was washed with deionized water (5×0.5 ml). The combined supernate and washes were extracted with ethyl acetate (3×0.5 ml) and concentrated under vacuum at 0° C. to provide 2.0 ml of a solution of 2-(4-methyl-1,2,3-triazol-1-yl)-carbapen-2-em-3-carboxylic acid and 2-(5-methyl-1,2,3-triazol-1-yl)-carbapen-2-em-3-carboxylic acid, UV λmax 295 nm quenched by addition of hydroxylamine hydrochloride and dipotassium hydrogen phosphate.

Workup

  1. washthe pellet was washed with deionized water (5×0.5 ml)
  2. extractionThe combined supernate and washes were extracted with ethyl acetate (3×0.5 ml)
  3. concentrationconcentrated under vacuum at 0° C.

Sources & evidence

ORD record
ord-44eff9adb1504adc87d45d509816fadc
Source dataset
uspto-grants-1990_01
Patent number
US04892869

Linked notes

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