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Acetamide, N-(trimethylsilyl)- → 7-[2-(2-Tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 34494
ノート
印刷プレビュー

反応式

HRID 34494 の反応式
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH:32]([F:34])[F:33])[C:27](O)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.S(Cl)(C)(=O)=O.[NH2:49][CH:50]1[C:67](=[O:68])[N:52]2[C:53]([C:64]([OH:66])=[O:65])=[C:54]([CH2:57][S:58][C:59]3[S:60][CH:61]=[N:62][N:63]=3)[CH2:55][S:56][C@H:51]12.C[Si](C)(C)NC(=O)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1.O>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH:32]([F:33])[F:34])[C:27]([NH:49][CH:50]2[C:67](=[O:68])[N:52]3[C:53]([C:64]([OH:66])=[O:65])=[C:54]([CH2:57][S:58][C:59]4[S:60][CH:61]=[N:62][N:63]=4)[CH2:55][S:56][C@H:51]23)=[O:28])[N:25]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 6

HCID 25989Acetamide, N-(trimethylsilyl)-HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 128891877-Amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acidHCID 536668022-(2-Tritylamino-4-thiazolyl)-2-difluoromethoxyimino-acetic acid

生成物 1

HCID 1317156677-[2-(2-Tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid収率 83.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-(2-tritylaminothiazol-4-yl)-2difluoromethoxyiminoacetic acid (syn isomer) (0.8 g) and diisopropylethylamine (0.43 g) in N,N-dimethylformamide (20 ml) was added mesyl chloride (0.38 g) at -20° C. and the mixture was stirred at the same temperature for 30 minutes to give an activated acid solution. To a solution of 7-amino-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (0.57 g) and N-trimethylsilylacetamide (1.8 g) in tetrahydrofuran (20 ml) was added the activated acid solution obtained above all at once at -10° C. After being stirred at the same temperature for an hour, the mixture was poured into water and adjusted to pH 2.5 with an aqueous solution of sodium bicarbonate. The precipitates were collected by filtration and washed with water to give 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.1 g).

後処理

  1. customto give an activated acid solution
  2. customobtained above all at once at -10° C
  3. stirringAfter being stirred at the same temperature for an hour
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water

出典と根拠

ORDレコード
ord-ce8d558ac081456ba95239ad58a7474c
出典データセット
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04761410

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート