Hydrochloric Acid → 1-(3-methylbutyryloxy)-2-methylpropyl 7beta-amino-3-[[[1-(2-dimethylaminoethyl)-1H-tetrazol-5-yl]thio]methyl]ceph-3-em-4-carboxylate dihydrochloride

HRID 4260Notes

Reaction equation

HRID 4260 reaction equation
[ClH:1].Cl.[NH2:3][C@@H:4]1[C:26](=[O:27])[N:6]2[C:7]([C:23]([OH:25])=[O:24])=[C:8]([CH2:11][S:12][C:13]3[N:17]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[N:16]=[N:15][N:14]=3)[CH2:9][S:10][C@H:5]12.C([O-])(=O)C.[K+].[CH3:33][CH:34]([CH3:44])[CH2:35][C:36]([O:38][CH:39](I)[CH:40]([CH3:42])[CH3:41])=[O:37].Cl>C(Cl)Cl.CN(C)C=O>[ClH:1].[ClH:1].[NH2:3][C@@H:4]1[C:26](=[O:27])[N:6]2[C:7]([C:23]([O:25][CH:39]([O:38][C:36](=[O:37])[CH2:35][CH:34]([CH3:44])[CH3:33])[CH:40]([CH3:42])[CH3:41])=[O:24])=[C:8]([CH2:11][S:12][C:13]3[N:17]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[N:16]=[N:15][N:14]=3)[CH2:9][S:10][C@H:5]12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 517044Potassium AcetateHCID 140301271-Iodo-2-methylpropyl 3-methylbutyrateHCID 703953067beta-amino-3-[[[1-(2-dimethylaminoethyl)-1H-tetrazol-5-yl]thio]methyl]ceph-3-em-4-carboxylic acid dihydrochloride

Product 1

HCID 704087121-(3-methylbutyryloxy)-2-methylpropyl 7beta-amino-3-[[[1-(2-dimethylaminoethyl)-1H-tetrazol-5-yl]thio]methyl]ceph-3-em-4-carboxylate dihydrochlorideYield 106%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 60 ml of dimethylformamide solution containing 4.22 g of 7β-amino-3-[[[1-(2-dimethylaminoethyl)-1H-tetrazol-5-yl]thio]methyl]ceph-3-em-4-carboxylic acid dihydrochloride is added 1.67 g of potassium acetate. The mixture is cooled to 0° C. With stirring, 5.0 g of 1-iodo-2-methylpropyl 3-methylbutyrate is added dropwise to the solution, followed by stirring at 0° C. for 5 minutes. The reaction mixture is poured into a mixture of 60 ml of methylene chloride and 60 ml of 0.1N-HCl and the aqueous layer is separated. The aqueous solution is adjusted to pH 6.0 with a saturated aqueous sodium bicarbonate solution and extracted with methylene chloride. To the methylene chloride solution is added water and the mixture is adjusted to pH 2.0 with 4N-HCl. The aqueous layer is separated and lyophilized to obtain 3.0 g of the title compound.

Workup

  1. stirringby stirring at 0° C. for 5 minutes
  2. customthe aqueous layer is separated
  3. extractionextracted with methylene chloride
  4. additionTo the methylene chloride solution is added water
  5. customThe aqueous layer is separated

Sources & evidence

ORD record
ord-44f5f31ec6e3435b87b6de372f03caf8
Source dataset
uspto-grants-1988_02
Patent number
US04725592

Reaction notes

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