1-Azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-, (4-nitrophenyl)methyl ester, (4R,5R,6S)- → HCID 22839796, compound

HRID 622436Notes

Reaction equation

HRID 622436 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[CH:7]([C:12]([O:14]CC3C=CC([N+]([O-])=O)=CC=3)=[O:13])[C:8](=O)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].Cl.[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([C:35](=[NH:38])[CH2:36][SH:37])[CH2:31][C:30]1=[O:39]>>[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([C:35](=[NH:38])[CH2:36][S:37][C:8]2[C@H:9]([CH3:10])[C@@H:5]3[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:25](=[O:26])[N:6]3[C:7]=2[C:12]([OH:14])=[O:13])[CH2:31][C:30]1=[O:39]

Participants

3

Reactant 2

HCID 98853021-Azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-, (4-nitrophenyl)methyl ester, (4R,5R,6S)-HCID 21293020HCID 21293020, compound

Product 1

HCID 22839796HCID 22839796, compoundYield 9.1%

Procedure

The procedure of Example 1(3) was repeated, except that 100 mg of p-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 90 mg of 2-(4-methyl-3-oxopiperazin-1-yl)-2-iminoethylmercaptan hydrochloride were used. After hydrogenation and filtration over "Celite" (Trade Mark) filter aid, the filtrate was extracted twice with 20 ml portions of diethyl ether. The aqueous phase was concentrated by evaporation under reduced pressure, and the residue was purified by chromatography through a Lobar column (Merck "LiChloprep RP-8", size B, two columns), eluted with 2% aqueous methanol, to give 10 mg of the title compound.

Workup

  1. filtrationAfter hydrogenation and filtration over "Celite" (Trade Mark)
  2. filtrationfilter aid
  3. extractionthe filtrate was extracted twice with 20 ml portions of diethyl ether
  4. concentrationThe aqueous phase was concentrated by evaporation under reduced pressure
  5. customthe residue was purified by chromatography through a Lobar column (Merck "LiChloprep RP-8", size B, two columns)
  6. washeluted with 2% aqueous methanol

Sources & evidence

ORD record
ord-9561b47bc70946deaf0118774fb90e61
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

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