Hydrochloric Acid → HCID 131713216, compound

HRID 648179Notes

Reaction equation

HRID 648179 reaction equation
[ClH: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>[ClH: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 313Hydrochloric AcidHCID 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 131713216HCID 131713216, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

61 ml of a 0.18 M HCl solution in CH2Cl2 (1.1 mol equivalent, prepared by introducing dry gaseous hydrogen chloride into dry CH2Cl2) are added to a solution, cooled to 0°, of 4.97 g of 7β-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid pivaloyloxymethyl ester (free base) in 50 ml of CH2Cl2. After stirring for 10 minutes, diethyl ether is 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 in a high vacuum at 30°. The crude hydrochloride is obtained as a pale beige powder which is dissolved in approximately 50 ml of CH2Cl2, concentrated slightly and left to stand overnight at approximately 5°. The compound that has crystallised out is filtered off, washed with a little CH2Cl2 and diethyl ether and dried as described above. The colourless 7β-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid pivaloyloxymethyl ester hydrochloride having a melting point of 187°-191° is obtained in syn-form.

Workup

  1. stirringThe mixture is stirred for a further 1/2 hour at 0°
  2. filtrationthe precipitate is filtered off
  3. washwashed with diethyl ether
  4. customdried in a high vacuum at 30°
  5. customThe crude hydrochloride is obtained as a pale beige powder which
  6. concentrationconcentrated slightly
  7. waitleft
  8. waitto stand overnight at approximately 5°
  9. customThe compound that has crystallised out
  10. filtrationis filtered off
  11. washwashed with a little CH2Cl2 and diethyl ether
  12. customdried

Sources & evidence

ORD record
ord-cd3ebc583ac742e9b6c238190465739c
Source dataset
uspto-grants-1983_10
Patent number
US04411897

Reaction notes

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