Triethylamine → 3-[(Acetyloxy)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 839143

Reaction equation

HRID 839143 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](NCC(O)=O)=[CH:5][CH:4]=1.ClC([O:17][CH2:18][CH:19](C)C)=O.[C:22]([O:25][CH2:26][C:27]1[CH2:34][S:33][CH:32]2[N:29]([C:30](=[O:36])[CH:31]2[NH2:35])[C:28]=1[C:37]([OH:39])=[O:38])(=[O:24])[CH3:23].C([N:42](CC)CC)C>>[C:22]([O:25][CH2:26][C:27]1[CH2:34][S:33][CH:32]2[N:29]([C:30](=[O:36])[CH:31]2[NH:35][C:18](=[O:17])[CH:19]([C:6]2[CH:5]=[CH:4][C:3]([CH2:2][Cl:1])=[CH:8][CH:7]=2)[NH2:42])[C:28]=1[C:37]([OH:39])=[O:38])(=[O:24])[CH3:23]

Participants

5

Reactant 4

HCID 8471Triethylamine2×HCID 137293-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 62365Isobutyl chloroformateHCID 22767740p-Chloromethylphenylglycine

Product 1

HCID 203258493-[(Acetyloxy)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 isobutyl chloroformate in the presence of triethylamine. The thus obtained mixed anhydride is reacted with the triethylamine salt of 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2carboxylic acid at 0° C for about 4 hours. The resulting product is isolated and the amine protecting group is removed by acid hydrolysis to give 3-[(acetyloxy)methyl]-7-[[2-[4-(chloromethyl)phenyl]-2-aminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2carboxylic acid.

Workup

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

Sources & evidence

ORD record
ord-52fec7966aa4461a8d8421e01142f209
Source dataset
uspto-grants-1978_06
Patent number
US04093804

Linked notes

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