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Sodium Bicarbonate → Oritavancin

HRID 1397115
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HRID 1397115 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

HCID 16136912Oritavancin

시약·촉매·용매 2

HCID 962
Water
용매
HCID 312751,4-Dioxane용매2회

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-115589a5fbe34b64b5e6aa30290383dc
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901072B2

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