Sodium Hydroxide → Micafungin sodium

HRID 518909Notes

Reaction equation

HRID 518909 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([C:24]([NH:26][C@@H:27]4[C:58](=[O:59])[NH:57][C@@H:56]([C@H:60]([OH:62])[CH3:61])[C:54](=[O:55])[N:53]5[C@@H:49]([CH2:50][C@@H:51]([OH:63])[CH2:52]5)[C:47](=[O:48])[NH:46][C@@H:45]([C@H:64]([OH:79])[C@@H:65]([OH:78])[C:66]5[CH:67]=[CH:68][C:69]([OH:77])=[C:70]([O:72][S:73]([OH:76])(=[O:75])=[O:74])[CH:71]=5)[C:43](=[O:44])[NH:42][C@@H:41]([C@H:80]([OH:85])[CH2:81][C:82]([NH2:84])=[O:83])[C:39](=[O:40])[N:38]5[C@@H:34]([C@@H:35]([OH:87])[C@@H:36]([CH3:86])[CH2:37]5)[C:32](=[O:33])[NH:31][C@H:30]([OH:88])[C@H:29]([OH:89])[CH2:28]4)=[O:25])=[CH:22][CH:23]=3)[CH:14]=2)=[CH:11][CH:12]=1.[OH-].[Na+:91]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([C:24]([NH:26][C@@H:27]4[C:58](=[O:59])[NH:57][C@@H:56]([C@H:60]([OH:62])[CH3:61])[C:54](=[O:55])[N:53]5[C@@H:49]([CH2:50][C@@H:51]([OH:63])[CH2:52]5)[C:47](=[O:48])[NH:46][C@@H:45]([C@H:64]([OH:79])[C@@H:65]([OH:78])[C:66]5[CH:67]=[CH:68][C:69]([OH:77])=[C:70]([O:72][S:73]([O-:76])(=[O:75])=[O:74])[CH:71]=5)[C:43](=[O:44])[NH:42][C@@H:41]([C@H:80]([OH:85])[CH2:81][C:82]([NH2:84])=[O:83])[C:39](=[O:40])[N:38]5[C@@H:34]([C@@H:35]([OH:87])[C@@H:36]([CH3:86])[CH2:37]5)[C:32](=[O:33])[NH:31][C@H:30]([OH:88])[C@H:29]([OH:89])[CH2:28]4)=[O:25])=[CH:22][CH:23]=3)[CH:14]=2)=[CH:9][CH:8]=1.[Na+:91]

Participants

3

Reactant 2

HCID 14798Sodium Hydroxide7×HCID 477468235114-32-6

Product 1

HCID 23666118Micafungin sodium

Procedure

According to the purification process for micafungin in WO2004014879, ion exchange was applied to 0.5 g of compound of formula I by using 50 ml of cation exchange resin UBK510L. The product was sampled and analyzed. HPLC purity was determined as 99.54%. Then, at room temperature, 0.1 mol/L NaOH solution was slowly added dropwise with stirring, until the pH of the solution achieving 4.0. The product was sampled and analyzed. HPLC purity was determined as 98.01% (See FIG. 2). 0.1 mol/L NaOH solution was continually added dropwise until the pH achieving 4.5. The produce was sampled and analyzed. HPLC purity was determined as 97.90%. 0.1 mol/L NaOH solution was continually added dropwise till the solution pH achieving 5.0. The product was sampled and analyzed. HPLC purity was determined as 97.81%. 0.1 mol/L NaOH solution was continually added dropwise till the solution pH achieving 5.5. The product was sampled and analyzed. HPLC purity was determined as 97.75%. 0.1 mol/L NaOH solution was continually added dropwise till the solution pH achieving 6.0. The product was sampled and analyzed. HPLC purity was determined as 97.67%. 0.1 mol/L NaOH solution was continually added dropwise until the solution pH achieving 6.5. The product was sampled and analyzed. HPLC purity was determined as 97.59%. 0.1 mol/L NaOH solution was continually added dropwise until the solution pH achieving 7.0. The product was sampled and analyzed. HPLC purity was determined as 97.30%, as shown in FIG. 3.

Workup

  1. aliquotThe product was sampled
  2. aliquotThe product was sampled
  3. aliquotThe produce was sampled
  4. aliquotThe product was sampled
  5. aliquotThe product was sampled
  6. aliquotThe product was sampled
  7. aliquotThe product was sampled
  8. aliquotThe product was sampled

Sources & evidence

ORD record
ord-4822208e81b84da592fcd93a9ee5b260
Source dataset
uspto-grants-2015_08
Patent number
US09115177B2

Reaction notes

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