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Hydrochloric Acid → benzhydryl (6R,7R)-7-[[(2Z)-2-(2-benzhydryloxy-2-oxoethoxy)imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-3-[2,2,2-triphenyl-1-(1H-triazol-4-ylsulfanyl)ethyl]sulfanyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1707461
ノート
印刷プレビュー

反応式

HRID 1707461 の反応式
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:26])[C@@H:24]([NH2:25])[C@H:21]3[S:20][CH2:19][C:18]=2[S:27][CH:28]([C:35]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[S:29][C:30]2[N:31]=[N:32][NH:33][CH:34]=2)=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:54]([NH:73][C:74]1[S:75][CH:76]=[C:77](/[C:79](=[N:83]/[O:84][CH2:85][C:86]([O:88][CH:89]([C:96]2[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=2)[C:90]2[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=2)=[O:87])/[C:80](O)=[O:81])[N:78]=1)([C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)([C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1.CN1CCOCC1.P(Cl)(Cl)(OC1C=CC=CC=1)=O.Cl>ClC.O>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:26])[C@@H:24]([NH:25][C:80](=[O:81])/[C:79](/[C:77]4[N:78]=[C:74]([NH:73][C:54]([C:55]5[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=5)([C:61]5[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=5)[C:67]5[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=5)[S:75][CH:76]=4)=[N:83]\[O:84][CH2:85][C:86]([O:88][CH:89]([C:96]4[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=4)[C:90]4[CH:91]=[CH:92][CH:93]=[CH:94][CH:95]=4)=[O:87])[C@H:21]3[S:20][CH2:19][C:18]=2[S:27][CH:28]([C:35]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[S:29][C:30]2[N:31]=[N:32][NH:33][CH:34]=2)=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 13038Phosphorodichloridic acid, phenyl esterHCID 13938984(2Z)-2-(2-benzhydryloxy-2-oxoethoxy)imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acidHCID 178511753HCID 178511753、化合物

生成物 1

HCID 88301232
benzhydryl (6R,7R)-7-[[(2Z)-2-(2-benzhydryloxy-2-oxoethoxy)imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-3-[2,2,2-triphenyl-1-(1H-triazol-4-ylsulfanyl)ethyl]sulfanyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
収率 73%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6327Methyl Chloride溶媒

反応条件

温度
-30 °C

実験手順

To a solution of 7β-amino-3-(trityl-1,2,3-triazol-4-ylthiomethyl-thio)-3-cephem-4-carboxylic acid diphenylmethyl ester (800 mg: 1.06 mMol.) and (Z)-2-(2-tritylaminothiazol-4-yl)-2-(diphenylmethoxycarbonylmethoxyimino)acetic acid (728 mg: 1.11 mMol.) in chloromethane (8 ml) cooling at -30° C. are added N-methylmorpholine (0.27 ml: 2.46 mMol.), phenyl dichlorophosphate (0.19 ml: 1.27 mMol.), and the mixture is stirred at -30° C. for 30 minutes. The reaction mixture is mixed with 10% hydrochloric acid (1 ml), diluted with water, and extracted with ethyl acetate. The extract washed with brine, dried over sodium sulfate, and concentrated. The residue is purified by silica gel chromatography (toluene: ethyl acetate=10:1) to give 7β-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-(diphenylmethoxycarbonylmethoxyimino)acetamido]-3-(trityl-1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (1.07 g) as yellow foam. Yield: 73%.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel chromatography (toluene: ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-c95db29e49bb467bb54b042b4f93de16
出典データセット
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05352792

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート