Potassium Carbonate → HCID 140360503, compound

HRID 1029694Notes

Reaction equation

HRID 1029694 reaction equation
[NH2:1][C@@H:2]([C:5]1[CH2:11][C@H:10]2[N:7]([C:8](=[O:15])[C@@H:9]2[C@H:12]([OH:14])[CH3:13])[C:6]=1[C:16]([OH:18])=[O:17])[CH2:3][NH2:4].Cl.[C:20](=N)(OCC)[CH3:21].C(=O)([O-])[O-].[K+].[K+]>O.O1CCCC1>[OH:14][C@@H:12]([C@H:9]1[C:8](=[O:15])[N:7]2[C@@H:10]1[CH2:11][C:5]([C@H:2]1[CH2:3][NH:4][C:20]([CH3:21])=[N:1]1)=[C:6]2[C:16]([OH:18])=[O:17])[CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 15117350HCID 15117350, compound

Product 1

HCID 140360503HCID 140360503, compoundYield 7.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5R,6S)-3-[(1S)-1,2-diaminoethyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (1.00 g) in a mixture of water (100 ml) and tetrahydrofuran (100 ml) was added portionwise ethyl acetimidate hydrochloride (1.00 g) under ice-cooling with stirring, keeping the pH between 8.0 and 8.5 with saturated aqueous potassium carbonate. After stirring for 2 hours, the mixture was concentrated under reduced pressure to be about 10 ml-volume. The aqueous solution was subjected to a column chromatography on silica gel (100 g) and eluted with a mixture of water and acetonitrile (6:4, V/V). The fractions containing the object compound were collected, concentrated under reduced pressure, and lyophilized to give a solid. A solution of the solid in water (10 ml) was subjected to a column chromatography on "Diaion HP-20" and eluted with water. The fractions containing the objected compound were collected, concentrated under reduced pressure, and lyophilized to give (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[(4S)-2-methyl-2-imidazolin-4-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.08 g) as a solid.

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 2 hours
  3. concentrationthe mixture was concentrated under reduced pressure
  4. washeluted with a mixture of water and acetonitrile (6:4, V/V)
  5. additionThe fractions containing the object compound
  6. customwere collected
  7. concentrationconcentrated under reduced pressure
  8. customto give a solid
  9. washeluted with water
  10. additionThe fractions containing the objected compound
  11. customwere collected
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ee95852c05247b5bc2e1c06a488567d
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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