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Pivaloyl chloride → 7-[2-(6-formamidopyridin-2-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 1982657
Notes
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Reaction equation

HRID 1982657 reaction equation
C(Cl)(=O)C(C)(C)C.[CH:8]([NH:10][C:11]1[N:16]=[C:15]([CH2:17][C:18]([OH:20])=O)[CH:14]=[CH:13][CH:12]=1)=[O:9].[NH2:21][CH:22]1[C:40](=[O:41])[N:24]2[C:25]([C:37]([OH:39])=[O:38])=[C:26]([CH2:29][S:30][C:31]3[N:35]([CH3:36])[N:34]=[N:33][N:32]=3)[CH2:27][S:28][C@H:23]12>C(Cl)Cl>[CH:8]([NH:10][C:11]1[N:16]=[C:15]([CH2:17][C:18]([NH:21][CH:22]2[C:40](=[O:41])[N:24]3[C:25]([C:37]([OH:39])=[O:38])=[C:26]([CH2:29][S:30][C:31]4[N:35]([CH3:36])[N:34]=[N:33][N:32]=4)[CH2:27][S:28][C@H:23]23)=[O:20])[CH:14]=[CH:13][CH:12]=1)=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 130208137-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacidHCID 130601732-(6-Formamidopyridin-2-yl)acetic acid

Product 1

HCID 886754457-[2-(6-formamidopyridin-2-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidYield 50.5%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
3×

Procedure

A solution of pivaloyl chloride (1.07 g.) in methylene chloride (3 ml.) was added to a solution of 2-(6-Formamidopyridin-2-yl)acetic acid (1.6 g.) and 1,5-diazabicyclo[5,4,0]undecene-5 (1.35 g.) in methylene chloride (25 ml.) at -20° to -25° C., and stirred at the same temperature for one hour [solution A]. On the other hand, a solution of 7-amino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (3.24 g.) and 1,5-diazabicyclo[5,4,0]undecene-5 (1.35 g.) in methylene chloride (60 ml.) was stirred at room temperature for 10 minutes. To the solution was added the above solution A at -20° to -25° C. and stirred at the same temperature for 1.5 hours. After removing the solvent from the resultant solution, ethyl acetate, water and sodium bicarbonate were added to the residue. The aqueous layer was separated and washed with ethyl acetate. Ethyl acetate (300 ml.) was added to the aqueous solution, adjusted to pH 2 to 3 with 5% hydrochloric acid, and then shaken sufficiently. The ethyl acetate layer was separated, washed with water and concentrated under reduced pressure to give 7-[2-(6-formamidopyridin-2-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (2.2 g.).

Workup

  1. customAfter removing the solvent from the resultant solution, ethyl acetate, water and sodium bicarbonate
  2. additionwere added to the residue
  3. customThe aqueous layer was separated
  4. washwashed with ethyl acetate
  5. additionEthyl acetate (300 ml.) was added to the aqueous solution
  6. stirringshaken sufficiently
  7. customThe ethyl acetate layer was separated
  8. washwashed with water
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a288b27e06fa4914b18952f7418bc2a0
Source dataset
uspto-grants-1986_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04596869

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes