Sodium Bicarbonate → Oritavancin

HRID 1397108Notes

Reaction equation

HRID 1397108 reaction equation
[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+]>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]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 70691404171099-57-3(Free base)

Product 1

HCID 16136912OritavancinYield 28.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To oritavancin bisphosphoric acid salt (5, 400 mg, 0.20 mmol) in 1,4-dioxane (10 mL) and H2O (10 mL) was added NaHCO3 (37.16 mg, 0.44 mmol) and the mixture was stirred until all of 5 had dissolved. A solution of 11 (98.94 mg, 0.24 mmol) in 1,4-dioxane (3 mL) was added and the resulting solution was stirred at room temperature for 2 days. The solvents were evaporated to dryness. The crude product was purified by C18 reversed phase chromatography on a Biotage™ flash chromatography system (10% to 60% MeCN in 0.05% aqueous TFA) to give 12 (102 mg, 24%) as a white solid: ESI-MS calculated for C100H114Cl3N11O32, 2088.4. found 2089.3 (M+H).

Workup

  1. dissolutionhad dissolved
  2. stirringthe resulting solution was stirred at room temperature for 2 days
  3. customThe solvents were evaporated to dryness
  4. customThe crude product was purified by C18 reversed phase chromatography on a Biotage™ flash chromatography system (10% to 60% MeCN in 0.05% aqueous TFA)

Sources & evidence

ORD record
ord-412f345dcb7c4e5daf83cc78af983790
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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