Triethylamine → HCID 22767745, compound

HRID 1111751Notes

Reaction equation

HRID 1111751 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8](NCC(O)=O)=[CH:7][CH:6]=1)=[N+:2]=[N-:3].ClC([O:19][CH2:20][CH:21](C)C)=O.[C:24]([O:27][CH2:28][C:29]1[CH2:36][S:35][CH:34]2[N:31]([C:32](=[O:38])[CH:33]2[NH2:37])[C:30]=1[C:39]([OH:41])=[O:40])(=[O:26])[CH3:25].C([N:44](CC)CC)C>>[C:24]([O:27][CH2:28][C:29]1[CH2:36][S:35][CH:34]2[N:31]([C:32](=[O:38])[CH:33]2[NH:37][C:20](=[O:19])[CH:21]([C:8]2[CH:7]=[CH:6][C:5]([CH2:4][N:1]=[N+:2]=[N-:3])=[CH:10][CH:9]=2)[NH2:44])[C:30]=1[C:39]([OH:41])=[O:40])(=[O:26])[CH3:25]

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 22767773HCID 22767773, compound

Product 1

HCID 22767745HCID 22767745, compound

Procedure

p-Azidomethylphenylglycine wherein the amino group is protected with tert-butoxycarbonyl is treated with isobutyl chloroformate in the presence of triethylamine. Equimolar amounts of the thus obtained mixed anhydride and the triethylamine salt of 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid are reacted at 0° C. for every 4 hours. The resluting product is isolated and the amine protecting group is removed by acid hydrolysis to give 3-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-aminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

Workup

  1. customEquimolar amounts of the thus obtained
  2. customThe resluting product is isolated
  3. customthe amine protecting group is removed by acid hydrolysis

Sources & evidence

ORD record
ord-0e2a27db48654803ba8b66f2463bad46
Source dataset
uspto-grants-1978_10
Patent number
US04118562

Reaction notes

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