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

反応式

HRID 839147 の反応式
[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

参加物

5

反応物 4

HCID 8471Triethylamine2 回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

生成物 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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a2dfcdbd52ed4c59a7405d7b36dd8a9a
出典データセット
uspto-grants-1978_06
特許番号
US04093804

関連ノート

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