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 255950Notes

Reaction equation

HRID 255950 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×

Conditions

Temperature
2.5 °C

Procedure

Teicoplanin A2 (10 g) is added to 1N 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 2N 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. stirringStirring
  3. temperatureis maintained for about 10 minutes
  4. filtrationafter which the precipitated solid is recovered by filtration
  5. washwashed with 20 ml of 2N HCl
  6. dry with materialwith ethyl ether, and dried overnight over potassium hydroxide pellets at room temperature

Sources & evidence

ORD record
ord-56b09b3690f3439caf77ca0aff376e9f
Source dataset
uspto-grants-1987_10
Patent number
US04699977

Reaction notes

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