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5-[(Aminooxy)methyl]-4,7-dichloro-2,2-diphenyl-1,3-benzodioxol hydrochloride → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(4,7-dichloro-2,2-diphenyl-1,3-benzodioxol-5-yl)methoxyimino]acetyl]amino]-3-[[5-(3,4-dihydroxyphenyl)pyrimidin-4-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1755862
ノート
印刷プレビュー

反応式

HRID 1755862 の反応式
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=O)[C:8]([NH:10][C@@H:11]2[C:18](=[O:19])[N:17]3[C@@H:12]2[S:13][CH2:14][C:15]([CH2:23][S:24][C:25]2[C:30]([C:31]4[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([OH:38])[CH:32]=4)=[CH:29][N:28]=[CH:27][N:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1.Cl.[NH2:41][O:42][CH2:43][C:44]1[CH:64]=[C:63]([Cl:65])[C:47]2[O:48][C:49]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[O:50][C:46]=2[C:45]=1[Cl:66]>CC(N(C)C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:41]/[O:42][CH2:43][C:44]2[CH:64]=[C:63]([Cl:65])[C:47]3[O:48][C:49]([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)([C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=4)[O:50][C:46]=3[C:45]=2[Cl:66])/[C:8]([NH:10][C@@H:11]2[C:18](=[O:19])[N:17]3[C@@H:12]2[S:13][CH2:14][C:15]([CH2:23][S:24][C:25]2[C:30]([C:31]4[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([OH:38])[CH:32]=4)=[CH:29][N:28]=[CH:27][N:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 199179675-[(Aminooxy)methyl]-4,7-dichloro-2,2-diphenyl-1,3-benzodioxol hydrochlorideHCID 86748847(6R,7R)-7-(2-amino-4-thiazoleglyoxylamido)-3-[[[5-(3,4-dihydroxyphenyl)-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

生成物 1

HCID 88420312(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(4,7-dichloro-2,2-diphenyl-1,3-benzodioxol-5-yl)methoxyimino]acetyl]amino]-3-[[5-(3,4-dihydroxyphenyl)pyrimidin-4-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
収率 98.4%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

(6R, 7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[5-(3,4-dihydroxyphenyl)-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (100 mg) (0.17 mmol) and 93 mg (0.22 mmol) of 5-[(aminooxy)methyl]-4,7-dichloro-2,2-diphenyl-1,3-benzodioxol hydrochloride are dissolved in 2 ml of absolute dimethylacetamide. After stirring at room temperature for 20 hours the solvent is distilled off in a high vacuum at room temperature. The residue is crystallized using diethyl ether. The product is filtered off under suction and washed with diethyl ether and water. There are obtained 160 mg of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[(4,7-dichloro-2,2-diphenyl-1,3-benzodioxol-5-yl)methoxy]imino]-acetamido]-3-[[[5-(3,4-dihydroxyphenyl)-4-pyrimidinyl]thio]-methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a beige powder after drying in a high vacuum at room temperature.

後処理

  1. distillationis distilled off in a high vacuum at room temperature
  2. customThe residue is crystallized
  3. filtrationThe product is filtered off under suction
  4. washwashed with diethyl ether and water

出典と根拠

ORDレコード
ord-028e55973d174d18b11d3794b28b35ff
出典データセット
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05438052

反応ノート

読み込み中…

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