Chlorotrimethylsilane → 7-Amino-3-(1-methyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate dihydrochloride

HRID 1607945Notes

Reaction equation

HRID 1607945 reaction equation
C([NH:9][CH:10]1[C:27](=[O:28])[N:12]2[C:13]([C:24]([O-:26])=[O:25])=[C:14]([CH2:17][N+:18]3([CH3:23])[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:15][S:16][C@H:11]12)(=O)C1C=CC=CC=1.C[Si]([Cl:33])(C)C.P(Cl)(Cl)(Cl)(Cl)[Cl:35].C(O)CCO>ClCCl.CN(C)C1C=CC=CC=1.C(O)C(C)C>[ClH:33].[ClH:35].[NH2:9][CH:10]1[C:27](=[O:28])[N:12]2[C:13]([C:24]([O-:26])=[O:25])=[C:14]([CH2:17][N+:18]3([CH3:23])[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:15][S:16][C@H:11]12

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 104421,3-PropanediolHCID 24819Phosphorus pentachlorideHCID 1317161257-Benzoylamino-3-(1-methyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate

Product 1

HCID 1317161277-Amino-3-(1-methyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate dihydrochloride

Reagents, catalysts & solvents 3

HCID 949N,N-DimethylanilineSolventHCID 6344DichloromethaneSolvent2×HCID 6560IsobutanolSolvent

Conditions

Temperature
-30 °C

Procedure

To a suspension of 7-benzoylamino-3-(1-methyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate (15 g) in a mixture of dichloromethane (300 ml) and N,N-dimethylaniline (41.7 g) was added dropwise trimethylsilyl chloride (31.2 g) at 5° C. After being stirred for 1 hour at 5°-10° C., the mixture was cooled up to -30° C. and then phosphorus pentachloride (11.9 g), was added thereto. After the mixture was stirred for 1 hour at -20°~-30° C., a mixture of isobutyl alcohol (21.2 g) and 1,3-propanediol (21.8 g) is dichloromethane (150 ml) cooled at -30° C. was added to the reaction mixture. The mixture was stirred for 1 day at room temperature to give a residue, which was collected by filtration, washed with dichloromethane, acetone and diisopropyl ether successively and dried over phosphorus pentoxide to give 7-amino-3-(1-methyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate dihydrochloride.

Workup

  1. stirringAfter the mixture was stirred for 1 hour at -20°~-30° C.
  2. temperaturecooled at -30° C.
  3. additionwas added to the reaction mixture
  4. stirringThe mixture was stirred for 1 day at room temperature
  5. customto give a residue, which
  6. filtrationwas collected by filtration
  7. washwashed with dichloromethane, acetone and diisopropyl ether successively
  8. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-886c498e8528474eb7fca18e84571504
Source dataset
uspto-grants-1989_09
Patent number
US04868174

Reaction notes

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