Hydrochloric Acid → (1S,2R,19R,22R,34S,37R,40R,52S)-2,64-bis[[(2R,3S,4R,5S,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]-22-amino-5,15-dichloro-26,31,44,49-tetrahydroxy-21,35,38,54,56,59-hexaoxo-47-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid

HRID 1249283Notes

Reaction equation

HRID 1249283 reaction equation
CCCCCCCC[CH2:9][C:10]([NH:12][C@H:13]1[C@H:18]([O:19][C:20]2[C:25]3[O:26][C:27]4[CH:32]=[CH:31][C:30]([C@@H:33]([O:113][C@@H:114]5[O:119][C@H:118]([CH2:120][OH:121])[C@@H:117]([OH:122])[C@H:116]([OH:123])[C@H:115]5[NH:124][C:125]([CH3:127])=[O:126])[C@@H:34]5[NH:54][C:52](=[O:53])[C@H:51]([NH:55][C:56]([C@@H:58]6[NH:59][C:60]([C@H:62]7[NH:93][C:91](=[O:92])[C@@H:81]([CH2:82][C:83]8[CH:89]=[CH:88][C:86]([O:87][C:21]=2[CH:22]=[C:23]6[CH:24]=3)=[C:85]([Cl:90])[CH:84]=8)[NH:80][C:78](=[O:79])[C@H:77]([NH2:94])[C:75]2=[CH:76][C:71](=[C:72]([OH:95])[CH:73]=[CH:74]2)[O:70][C:65]2=[CH:66][C:67]([OH:69])=[CH:68][C:63]7=[CH:64]2)=[O:61])=[O:57])[C:49]2=[CH:50][C:45](=[C:46]([OH:96])[CH:47]=[CH:48]2)[C:44]2[C:39](=[CH:40][C:41]([OH:109])=[CH:42][C:43]=2[O:97][C@H:98]2[O:103][C@H:102]([CH2:104][OH:105])[C@@H:101]([OH:106])[C@H:100]([OH:107])[C@@H:99]2[OH:108])[C@H:38]([C:110]([OH:112])=[O:111])[NH:37][C:35]5=[O:36])=[CH:29][C:28]=4[Cl:128])[O:17][C@H:16]([CH2:129][OH:130])[C@@H:15]([OH:131])[C@@H:14]1[OH:132])=[O:11].Cl.C(OCC)C>C(O)CCCCCCC>[CH3:9][C:10]([NH:12][C@@H:13]1[C@H:18]([O:19][C:20]2[C:25]3[O:26][C:27]4[CH:32]=[CH:31][C:30]([C@@H:33]([O:113][C@@H:114]5[O:119][C@@H:118]([CH2:120][OH:121])[C@@H:117]([OH:122])[C@H:116]([OH:123])[C@@H:115]5[NH:124][C:125]([CH3:127])=[O:126])[C@@H:34]5[NH:54][C:52](=[O:53])[C@H:51]([NH:55][C:56]([C@@H:58]6[NH:59][C:60]([C@H:62]7[NH:93][C:91](=[O:92])[C@@H:81]([CH2:82][C:83]8[CH:89]=[CH:88][C:86]([O:87][C:21]=2[CH:22]=[C:23]6[CH:24]=3)=[C:85]([Cl:90])[CH:84]=8)[NH:80][C:78](=[O:79])[C@H:77]([NH2:94])[C:75]2[CH:74]=[CH:73][C:72]([OH:95])=[C:71]([CH:76]=2)[O:70][C:65]2=[CH:64][C:63]7=[CH:68][C:67]([OH:69])=[CH:66]2)=[O:61])=[O:57])[C:49]2[CH:48]=[CH:47][C:46]([OH:96])=[C:45]([CH:50]=2)[C:44]2[C:43]([O:97][C@H:98]3[O:103][C@H:102]([CH2:104][OH:105])[C@@H:101]([OH:106])[C@@H:100]([OH:107])[C@@H:99]3[OH:108])=[CH:42][C:41]([OH:109])=[CH:40][C:39]=2[C@@H:38]([C:110]([OH:112])=[O:111])[NH:37][C:35]5=[O:36])=[CH:29][C:28]=4[Cl:128])[O:17][C@@H:16]([CH2:129][OH:130])[C@@H:15]([OH:131])[C@@H:14]1[OH:132])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 16131923(1S,2R,19R,22R,34S,37R,40R,52R)-2-((2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-22-azaniumyl-5,15-dichloro-64-((2S,3R,4R,5S,6R)-3-(decanoylamino)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-26,31,44,49-tetrahydroxy-21,35,38,54,56,59-hexaoxo-47-((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo(38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51)hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylate

Product 1

HCID 73348316(1S,2R,19R,22R,34S,37R,40R,52S)-2,64-bis[[(2R,3S,4R,5S,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]-22-amino-5,15-dichloro-26,31,44,49-tetrahydroxy-21,35,38,54,56,59-hexaoxo-47-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid

Reagents, catalysts & solvents 1

HCID 9571-OctanolSolvent2×

Conditions

Temperature
65 °C

Procedure

To a suspension of 5 g of teicoplanin complex (i.e. the antibiotic complex containing teichomycin factors A1, A2 and A3, as obtained by fermentation of strain ATCC 31121 according to U.S. Pat. No. 4,239,751) in 80 ml of 1-octanol, are added 20 ml of 37% (w/v) aqueous HCl at about 40° C. and the mixture is heated at 65° C. and stirred under vacuum for 13 hours. During the reaction time, additions of a mixture of 5 ml of 37% aqueous HCl and 15 ml of 1-octanol are repeated every two hours. At the end of the reaction, the mixture is cooled to room temperature and then poured into 800 ml of ethyl ether. The solid which precipitates is washed with acetone and dried under vacuum at 40° C. overnight. The crude product thus obtained is then worked up according to the last part of Example 4, yielding 0.6 g of substantially pure deglucoteicoplanin.

Workup

  1. additionTo a suspension of 5 g of teicoplanin complex (i.e. the antibiotic complex
  2. customas obtained by fermentation of strain ATCC 31121 according to U.S
  3. waitare repeated every two hours
  4. customAt the end of the reaction
  5. temperaturethe mixture is cooled to room temperature
  6. customThe solid which precipitates
  7. washis washed with acetone
  8. customdried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-2e32e86af1804bb081f944ad0d15b323
Source dataset
uspto-grants-1986_12
Patent number
US04629781

Reaction notes

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