Hydrogen Bromide → HCID 131713218, compound

HRID 648180Notes

Reaction equation

HRID 648180 reaction equation
[BrH:1].[C:2]([O:8][CH2:9][O:10][C:11]([C:13]1[N:18]2[C:19](=[O:34])[C@@H:20]([NH:21][C:22](=[O:33])[C:23]([C:27]3[N:28]=[C:29]([NH2:32])[S:30][CH:31]=3)=[N:24][O:25][CH3:26])[C@H:17]2[S:16][CH2:15][CH:14]=1)=[O:12])(=[O:7])[C:3]([CH3:6])([CH3:5])[CH3:4].C(OCC)C>C(Cl)Cl>[BrH:1].[C:2]([O:8][CH2:9][O:10][C:11]([C:13]1[N:18]2[C:19](=[O:34])[C@@H:20]([NH:21][C:22](=[O:33])[C:23]([C:27]3[N:28]=[C:29]([NH2:32])[S:30][CH:31]=3)=[N:24][O:25][CH3:26])[C@H:17]2[S:16][CH2:15][CH:14]=1)=[O:12])(=[O:7])[C:3]([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 1317132175-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (6R-trans)-

Product 1

HCID 131713218HCID 131713218, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.72 ml of a 0.46 M HBr solution in CH2Cl2 (1.25 mol equivalents) are added, while stirring, to a solution, cooled with ice, of 497 mg of 7β-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid pivaloyloxymethyl ester (free base) in 5 ml of CH2Cl2. After stirring for 10 minutes, 35 ml of diethyl ether are added to the solution and a precipitate forms. The mixture is stirred for a further 1/2 hour at 0°, the precipitate is filtered off, washed with diethyl ether and dried on a suction filter. The resulting faintly orange powder is dissolved in 2.5 ml of CH2Cl2, whereupon the product recrystallises. After the addition of 5 ml of CH2Cl2, the mixture is stirred for one hour while cooling with ice. Filtration, washing of the resulting crystals with CH2Cl2 and diethyl ether and drying in a high vacuum yield the 7β-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid pivaloyloxymethyl ester hydrobromide in syn-form having a melting point of 215° (with decomposition).

Workup

  1. stirringAfter stirring for 10 minutes
  2. stirringThe mixture is stirred for a further 1/2 hour at 0°
  3. filtrationthe precipitate is filtered off
  4. washwashed with diethyl ether
  5. customdried on a suction
  6. filtrationfilter
  7. dissolutionThe resulting faintly orange powder is dissolved in 2.5 ml of CH2Cl2, whereupon the product
  8. customrecrystallises
  9. additionAfter the addition of 5 ml of CH2Cl2
  10. stirringthe mixture is stirred for one hour
  11. temperaturewhile cooling with ice
  12. filtrationFiltration
  13. washwashing of the resulting crystals with CH2Cl2 and diethyl ether
  14. customdrying in a high vacuum

Sources & evidence

ORD record
ord-058c8c635736432ab8696cefeeada6ae
Source dataset
uspto-grants-1983_10
Patent number
US04411897

Reaction notes

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