Teicoplanin A 2 → (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 1906239Notes

Reaction equation

HRID 1906239 reaction equation
CCCCC/C=C/C[CH2:9][C:10]([NH:12][CH:13]1[CH:18]([O:19][C:20]2[C:25]3[O:26][C:27]4[CH:32]=[CH:31][C:30]([CH:33]([O:116][CH:117]5[O:122][CH:121]([CH2:123][OH:124])[CH:120]([OH:125])[CH:119]([OH:126])[CH:118]5[NH:127][C:128]([CH3:130])=[O:129])[CH:34]5[NH:54][C:52](=[O:53])[CH:51]([NH:55][C:56]([CH:58]6[NH:59][C:60]([CH:62]7[NH:95][C:93](=[O:94])[CH:82]([CH:83](O)[C:84]8[CH:90]=[CH:89][C:87]([O:88][C:21]=2[CH:22]=[C:23]6[CH:24]=3)=[C:86]([Cl:91])[CH:85]=8)[NH:81][C:79](=[O:80])[CH:78]([NH2:96])[C:76]2=[CH:77][C:72](=[C:73]([OH:97])[CH:74]=[CH:75]2)[O:71][C:65]2=[C:66](C)[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:98])[CH:47]=[CH:48]2)[C:44]2[C:39](=[CH:40][C:41]([OH:111])=[CH:42][C:43]=2[O:99][CH:100]2[O:105][CH:104]([CH2:106][OH:107])[CH:103]([OH:108])[CH:102]([OH:109])[CH:101]2[OH:110])[CH:38]([C:112]([O:114]C)=[O:113])[NH:37][C:35]5=[O:36])=[CH:29][C:28]=4[Cl:131])[O:17][CH:16]([CH2:132][OH:133])[CH:15]([OH:134])[CH:14]1[OH:135])=[O:11]>Cl>[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:116][C@@H:117]5[O:122][C@@H:121]([CH2:123][OH:124])[C@@H:120]([OH:125])[C@H:119]([OH:126])[C@@H:118]5[NH:127][C:128]([CH3:130])=[O:129])[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:95][C:93](=[O:94])[C@@H:82]([CH2:83][C:84]8[CH:90]=[CH:89][C:87]([O:88][C:21]=2[CH:22]=[C:23]6[CH:24]=3)=[C:86]([Cl:91])[CH:85]=8)[NH:81][C:79](=[O:80])[C@H:78]([NH2:96])[C:76]2[CH:75]=[CH:74][C:73]([OH:97])=[C:72]([CH:77]=2)[O:71][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:98])=[C:45]([CH:50]=2)[C:44]2[C:43]([O:99][C@H:100]3[O:105][C@H:104]([CH2:106][OH:107])[C@@H:103]([OH:108])[C@@H:102]([OH:109])[C@@H:101]3[OH:110])=[CH:42][C:41]([OH:111])=[CH:40][C:39]=2[C@@H:38]([C:112]([OH:114])=[O:113])[NH:37][C:35]5=[O:36])=[CH:29][C:28]=4[Cl:131])[O:17][C@@H:16]([CH2:132][OH:133])[C@@H:15]([OH:134])[C@@H:14]1[OH:135])=[O:11]

Participants

3

Reactant 1

HCID 16132315Teicoplanin A 2

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 313Hydrochloric AcidSolvent2×

Procedure

Teicoplanin A2 (10 g) is added to 1 N hydrochloric acid (150 ml) preheated to 80° C. while stirring. After about 45 minutes the reaction mixture is cooled to 0°-5° C. and 37% hydrochloric acid (30 ml) is added. Stirring is maintained for about 10 minutes, after which the precipitated solid is recovered by filtration, washed with 20 ml of 2 N HCl, then with ethyl ether, and dried overnight over potassium hydroxide pellets at room temperature, resulting in the crude product of the title (8.3 g).

Workup

  1. custompreheated to 80° C.
  2. temperatureAfter about 45 minutes the reaction mixture is cooled to 0°-5° C.
  3. stirringStirring
  4. temperatureis maintained for about 10 minutes
  5. filtrationafter which the precipitated solid is recovered by filtration
  6. washwashed with 20 ml of 2 N HCl
  7. dry with materialwith ethyl ether, and dried overnight over potassium hydroxide pellets at room temperature

Sources & evidence

ORD record
ord-29db6b1240c341fc92036493f5165428
Source dataset
uspto-grants-1987_03
Patent number
US04650855

Reaction notes

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