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 2398965

反応式

HRID 2398965 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.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]

参加物

5

反応物 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

生成物 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

実験手順

p-Chloromethylphenylglycine wherein the amino group is protected with tert-butoxycarbonyl is treated with isobutyl chloroformate in the presenceof 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 4 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]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid pivalyloxymethyl ester.

後処理

  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

出典と根拠

ORDレコード
ord-0a9da20f39f24e82b91c79db8ab4c1b8
出典データセット
uspto-grants-1977_05
特許番号
US04026887

関連ノート

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