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Sodium Bicarbonate → Oritavancin

HRID 1397115
ノート
印刷プレビュー

反応式

HRID 1397115 の反応式
[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@@H:100]3[NH:101][C:102](=[O:103])[C@@H:81]([C:82]4[CH:83]=[CH:84][C:85]([OH:107])=[C:86]([C:88]5[C:93]([OH:94])=[CH:92][C:91]([OH:95])=[CH:90][C:89]=5[C@@H:96]([C:104]([OH:106])=[O:105])[NH:97][C:98]3=[O:99])[CH:87]=4)[NH:80][C:78](=[O:79])[C@H:77]3[C:20]4=[CH:21][C:22]([O:60][C:61]5[CH:62]=[CH:63][C:64]([C@@H:68]([OH:122])[C@@H:69]([NH:112][C:113]([C@H:115]([NH:120][CH3:121])[CH2:116][CH:117]([CH3:119])[CH3:118])=[O:114])[C:70]([NH:72][C@@H:73]([CH2:108][C:109]([NH2:111])=[O:110])[C:74]([NH:76]3)=[O:75])=[O:71])=[CH:65][C:66]=5[Cl:67])=[C:23]([O:24][C@@H:25]3[O:30][C@H:29]([CH2:31][OH:32])[C@@H:28]([OH:33])[C@H:27]([OH:34])[C@H:26]3[O:35][C@@H:36]3[O:41][C@@H:40]([CH3:42])[C@H:39]([OH:43])[C@:38]([NH:45][CH2:46][C:47]5[CH:48]=[CH:49][C:50]([C:53]6[CH:54]=[CH:55][C:56]([Cl:59])=[CH:57][CH:58]=6)=[CH:51][CH:52]=5)([CH3:44])[CH2:37]3)[C:18](=[CH:19]4)[O:17][C:13]3=[C:14]([Cl:16])[CH:15]=[C:10]2[CH:11]=[CH:12]3)[CH2:5][C@@:4]([NH2:124])([CH3:123])[C@H:3]1[OH:125].OP(O)(O)=O.C([O-])(O)=O.[Na+].C(=O)([O-])ON1C(=O)CCC1=O>O1CCOCC1.O>[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@@H:100]3[NH:101][C:102](=[O:103])[C@@H:81]([C:82]4[CH:83]=[CH:84][C:85]([OH:107])=[C:86]([C:88]5[C:93]([OH:94])=[CH:92][C:91]([OH:95])=[CH:90][C:89]=5[C@@H:96]([C:104]([OH:106])=[O:105])[NH:97][C:98]3=[O:99])[CH:87]=4)[NH:80][C:78](=[O:79])[C@H:77]3[C:20]4=[CH:21][C:22]([O:60][C:61]5[CH:62]=[CH:63][C:64]([C@@H:68]([OH:122])[C@@H:69]([NH:112][C:113]([C@H:115]([NH:120][CH3:121])[CH2:116][CH:117]([CH3:118])[CH3:119])=[O:114])[C:70]([NH:72][C@@H:73]([CH2:108][C:109]([NH2:111])=[O:110])[C:74]([NH:76]3)=[O:75])=[O:71])=[CH:65][C:66]=5[Cl:67])=[C:23]([O:24][C@@H:25]3[O:30][C@H:29]([CH2:31][OH:32])[C@@H:28]([OH:33])[C@H:27]([OH:34])[C@H:26]3[O:35][C@@H:36]3[O:41][C@@H:40]([CH3:42])[C@H:39]([OH:43])[C@:38]([NH:45][CH2:46][C:47]5[CH:52]=[CH:51][C:50]([C:53]6[CH:58]=[CH:57][C:56]([Cl:59])=[CH:55][CH:54]=6)=[CH:49][CH:48]=5)([CH3:44])[CH2:37]3)[C:18](=[CH:19]4)[O:17][C:13]3=[C:14]([Cl:16])[CH:15]=[C:10]2[CH:11]=[CH:12]3)[CH2:5][C@@:4]([NH2:124])([CH3:123])[C@H:3]1[OH:125]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 22239412(2,5-Dioxopyrrolidin-1-yl) carbonateHCID 70691404171099-57-3(Free base)

生成物 1

HCID 16136912Oritavancin

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 312751,4-Dioxane溶媒2 回

実験手順

To oritavancin bisphosphoric acid salt (5, 180 mg, 0.0905 mmol) in 1,4-dioxane (2 mL) and H2O (2 mL) was added NaHCO3 (25 mg, 0.29 mmol) and the mixture was stirred until all of 5 had dissolved. A solution of 34 (135 mg, 0.164 mmol) in 1,4-dioxane (3 mL) was added and the resulting solution was stirred at room temperature overnight. The product was precipitated by the addition of H2O and collected by filtration. The crude product was purified by C18 reversed phase chromatography on a Biotage™ flash chromatography system (30% to 80% MeCN in 0.2% TEA/phosphate pH 3) to give 37 (135 mg, 55%, based on the di-phosphoric acid salt) as a white solid: ESI-MS (M+2H) calculated for C120H157Cl3N14O38 1256.0. found 1255.4

後処理

  1. dissolutionhad dissolved
  2. stirringthe resulting solution was stirred at room temperature overnight
  3. customThe product was precipitated by the addition of H2O
  4. filtrationcollected by filtration
  5. customThe crude product was purified by C18 reversed phase chromatography on a Biotage™ flash chromatography system (30% to 80% MeCN in 0.2% TEA/phosphate pH 3)

出典と根拠

ORDレコード
ord-115589a5fbe34b64b5e6aa30290383dc
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08901072B2

反応ノート

読み込み中…

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