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 pivalyloxymethyl ester

HRID 839148Notes

Reaction equation

HRID 839148 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:28][CH2:29][O:30][C:31]([C:33]1[N:34]2[CH:37]([S:38][CH2:39][C:40]=1[CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH:36]([NH2:46])[C:35]2=[O:47])=[O:32])(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24].C([N:50](CC)CC)C>>[C:22]([O:28][CH2:29][O:30][C:31]([C:33]1[N:34]2[CH:37]([S:38][CH2:39][C:40]=1[CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH:36]([NH:46][C:18](=[O:17])[CH:19]([C:6]1[CH:5]=[CH:4][C:3]([CH2:2][Cl:1])=[CH:8][CH:7]=1)[NH2:50])[C:35]2=[O:47])=[O:32])(=[O:27])[C:23]([CH3:25])([CH3:26])[CH3:24]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 128109063-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid pivalyloxymethyl esterHCID 22767740p-Chloromethylphenylglycine

Product 1

HCID 541348743-[(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 pivalyloxymethyl ester

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 3[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid pivalyloxymethyl ester at 0° C for about 3 hours. The resulting product is isolated, and the amine protecting group is removed by acid hydrolysis by treating the product with difluoroacetic acid for 5 minutes at room temperature to give 3-[(acetyloxy)methyl]-7[[2-[4-(chloromethyl)phenyl]-2-aminoacetyl]amino]-8oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid pivalyloxymethyl ester.

Workup

  1. customThe thus obtained
  2. customThe resulting product is isolated
  3. customthe amine protecting group is removed by acid hydrolysis
  4. additionby treating the product with difluoroacetic acid for 5 minutes at room temperature

Sources & evidence

ORD record
ord-3abed74665a0414e92ca52182cfbe613
Source dataset
uspto-grants-1978_06
Patent number
US04093804

Reaction notes

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