Bacitracin → Bacitracin Zn Lasalocid

HRID 2309224Notes

Reaction equation

HRID 2309224 reaction equation
[Zn:1].[CH3:2][CH2:3][C@@H:4]([C:23]([C@H:25]([C@@H:27]([OH:43])[C@@H:28]([CH2:30][CH2:31][C:32]1[CH:33]=[CH:34][C:35]([CH3:42])=[C:36]([OH:41])[C:37]=1[C:38]([OH:40])=[O:39])[CH3:29])[CH3:26])=[O:24])[C@H:5]1[O:9][C@@:8]([C@@H:12]2[O:17][C@@H:16]([CH3:18])[C@@:15]([OH:21])([CH2:19][CH3:20])[CH2:14][CH2:13]2)([CH2:10][CH3:11])[CH2:7][C@@H:6]1[CH3:22].[CH3:44][CH2:45][C@@H:46]([C@@H:48]1[NH:79][C:77](=[O:78])[C@@H:76]([CH2:80][CH2:81][CH2:82][NH2:83])[NH:75][C:73](=[O:74])[C@@H:72]([NH:84][C:85]([C@@H:87]([NH:92][C:93]([C@H:95]([NH:101][C:102]([C@@H:104]([NH:109][C:110]([C@H:112]2[N:116]=[C:115]([C@@H:117]([NH2:122])[C@H:118]([CH2:120][CH3:121])[CH3:119])[S:114][CH2:113]2)=[O:111])[CH2:105][CH:106]([CH3:108])[CH3:107])=[O:103])[CH2:96][CH2:97][C:98]([OH:100])=[O:99])=[O:94])[C@H:88]([CH2:90][CH3:91])[CH3:89])=[O:86])[CH2:71][CH2:70][CH2:69][CH2:68][NH:67][C:65](=[O:66])[C@H:64]([CH2:123][C:124]([NH2:126])=[O:125])[NH:63][C:61](=[O:62])[C@@H:60]([CH2:127][C:128]([OH:130])=[O:129])[NH:59][C:57](=[O:58])[C@H:56]([CH2:131][C:132]2[NH:136][CH:135]=[N:134][CH:133]=2)[NH:55][C:53](=[O:54])[C@@H:52]([CH2:137][C:138]2[CH:139]=[CH:140][CH:141]=[CH:142][CH:143]=2)[NH:51][C:49]1=[O:50])[CH3:47]>CO>[CH3:44][CH2:45][C@@H:46]([C@@H:48]1[NH:79][C:77](=[O:78])[C@@H:76]([CH2:80][CH2:81][CH2:82][NH2:83])[NH:75][C:73](=[O:74])[C@@H:72]([NH:84][C:85]([C@@H:87]([NH:92][C:93]([C@H:95]([NH:101][C:102]([C@@H:104]([NH:109][C:110]([C@H:112]2[N:116]=[C:115]([C@@H:117]([NH2:122])[C@H:118]([CH2:120][CH3:121])[CH3:119])[S:114][CH2:113]2)=[O:111])[CH2:105][CH:106]([CH3:107])[CH3:108])=[O:103])[CH2:96][CH2:97][C:98]([OH:100])=[O:99])=[O:94])[C@H:88]([CH2:90][CH3:91])[CH3:89])=[O:86])[CH2:71][CH2:70][CH2:69][CH2:68][NH:67][C:65](=[O:66])[C@H:64]([CH2:123][C:124]([NH2:126])=[O:125])[NH:63][C:61](=[O:62])[C@@H:60]([CH2:127][C:128]([OH:130])=[O:129])[NH:59][C:57](=[O:58])[C@H:56]([CH2:131][C:132]2[NH:136][CH:135]=[N:134][CH:133]=2)[NH:55][C:53](=[O:54])[C@@H:52]([CH2:137][C:138]2[CH:139]=[CH:140][CH:141]=[CH:142][CH:143]=2)[NH:51][C:49]1=[O:50])[CH3:47].[Zn:1].[CH3:2][CH2:3][C@@H:4]([C:23]([C@H:25]([C@@H:27]([OH:43])[C@@H:28]([CH2:30][CH2:31][C:32]1[CH:33]=[CH:34][C:35]([CH3:42])=[C:36]([OH:41])[C:37]=1[C:38]([OH:40])=[O:39])[CH3:29])[CH3:26])=[O:24])[C@H:5]1[O:9][C@@:8]([C@@H:12]2[O:17][C@@H:16]([CH3:18])[C@@:15]([OH:21])([CH2:19][CH3:20])[CH2:14][CH2:13]2)([CH2:10][CH3:11])[CH2:7][C@@H:6]1[CH3:22]

Participants

4

Reactant 2

HCID 10909430BacitracinHCID 86741799ZINC lasalocid

Product 1

HCID 86741798Bacitracin Zn Lasalocid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.5 g of zinc lasalocid in 50 ml of methanol was stirred and 3.0 g of regular bacitracin was added. The mixture was stirred to dissolve all solids. The resulting solution was set aside and held at ambient temperature for 24 hours. The precipitated complex was isolated, rinsed with methanol, and dried; wt. 2.3 g. Analytical sample was recrystallized from methylene chloride and methanol. The crude complex was dissolved at room temperature in a mixture of 90% methylene chloride and 10% methanol. Solution was filtered to remove traces of insoluble and the complex recovered from the filtrate by the slow addition of additional methanol. The complex was also recovered from the filtrate by the slow removal of the methylene chloride under reduced pressure at 30°-35° C.

Workup

  1. dissolutionto dissolve all solids
  2. customThe precipitated complex was isolated
  3. washrinsed with methanol
  4. customdried
  5. customAnalytical sample was recrystallized from methylene chloride and methanol
  6. dissolutionThe crude complex was dissolved at room temperature in a mixture of 90% methylene chloride and 10% methanol
  7. filtrationSolution was filtered
  8. customto remove traces of insoluble and the complex
  9. customrecovered from the filtrate by the slow addition of additional methanol
  10. customThe complex was also recovered from the filtrate by the slow removal of the methylene chloride under reduced pressure at 30°-35° C.

Sources & evidence

ORD record
ord-35aaa235f1614b6989b5041b56da8bd3
Source dataset
uspto-grants-1987_09
Patent number
US04693992

Reaction notes

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