Water → (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 1249287Notes

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].O>Cl.FC(F)(F)C(O)C(F)(F)F>[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

Conditions

Temperature: 70 °C

Procedure

10 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; the water content determined by Karl-Fischer method is 10.5% by weight) is suspended in 100 ml of 0.5 N hydrogen chloride solution in 1,1,1,3,3,3-hexafluoro-2-propanol and the suspension is heated at 70° C. with stirring while continuously bubbling anhydrous hydrogen chloride for 20 hours. Then the reaction mixture is worked up as in Example 11 yielding 3.8 g of substantially pure deglucoteicoplanin. From 0.8 g of this sample are obtained 0.5 g of crystalline pure deglucoteicoplanin by employing the procedure described in the last part of Example 1.

Workup

customas obtained by fermentation of strain ATCC 31121 according to U.S
customFrom 0.8 g of this sample are obtained 0.5 g of crystalline pure deglucoteicoplanin

Sources & evidence

ORD record: ord-27834bb64dfa42958d21ae3ad484d773
Source dataset: uspto-grants-1986_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04629781

Reaction notes

Loading…