Triethylamine → 3-[(2-Methyl-1,3,4-thiadiazol-5-ylthio)methyl]-7-[[2-[4-(chloromethyl)phenyl]-2-aminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 839147

Reaction equation

HRID 839147 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](NCC(O)=O)=[CH:5][CH:4]=1.[CH2:14]([O:18]C(Cl)=O)[CH:15](C)C.[CH3:22][C:23]1[S:24][C:25]([S:28][CH2:29][C:30]2[CH2:37][S:36][CH:35]3[N:32]([C:33](=[O:39])[CH:34]3[NH2:38])[C:31]=2[C:40]([OH:42])=[O:41])=[N:26][N:27]=1.C([N:45](CC)CC)C>>[CH3:22][C:23]1[S:24][C:25]([S:28][CH2:29][C:30]2[CH2:37][S:36][CH:35]3[N:32]([C:33](=[O:39])[CH:34]3[NH:38][C:14](=[O:18])[CH:15]([C:6]3[CH:5]=[CH:4][C:3]([CH2:2][Cl:1])=[CH:8][CH:7]=3)[NH2:45])[C:31]=2[C:40]([OH:42])=[O:41])=[N:26][N:27]=1

Participants

5

Reactant 4

HCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 31498227-Amino-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 22767740p-Chloromethylphenylglycine

Product 1

HCID 203258583-[(2-Methyl-1,3,4-thiadiazol-5-ylthio)methyl]-7-[[2-[4-(chloromethyl)phenyl]-2-aminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Procedure

p-Chloromethylphenylglycine wherein the amino group is protected with tert-butoxycarbonyl is treated with isobutylchloroformate in the presence of triethylamine. The thus obtained anhydride is reacted with the triethylamine salt of 3-[(2-methyl-1,3,4-thiadiazol-5-ylthio)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid at 0° C for about 4 hours. The resulting product is isolated, and the amine protecting group is removed by acid hydrolysis and the amine protecting group is removed by acid hydrolysis to give 3-[(2-methyl-1,3,4-thiadiazol-5-ylthio)methyl]-7-[[2-[4-(chloromethyl)phenyl]-2-aminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

Workup

  1. customThe resulting product is isolated
  2. customthe amine protecting group is removed by acid hydrolysis
  3. customthe amine protecting group is removed by acid hydrolysis

Sources & evidence

ORD record
ord-a2dfcdbd52ed4c59a7405d7b36dd8a9a
Source dataset
uspto-grants-1978_06
Patent number
US04093804

Linked notes

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