Triethylamine → Vancomycin

HRID 392028Notes

Reaction equation

HRID 392028 reaction equation
C(N(CC)CC)C.[CH3:8][C@@H:9]1[O:14][C@@H:13]([O:15][C@H:16]2[C@H:21]([O:22][C:23]3[C:24]4[O:78][C:74]5=[C:75]([Cl:77])[CH:76]=[C:71]([CH:72]=[CH:73]5)[C@@H:70]([OH:79])[C@@H:69]5[NH:80][C:81](=[O:82])[C@@H:50]([C:51]6[CH:52]=[CH:53][C:54]([OH:86])=[C:55]([C:57]7[C:62]([OH:63])=[CH:61][C:60]([OH:64])=[CH:59][C:58]=7[C@@H:65]([C:83]([OH:85])=[O:84])[NH:66][C:67]5=[O:68])[CH:56]=6)[NH:49][C:47](=[O:48])[C@H:46]5[C:26](=[CH:27][C:28]=3[O:29][C:30]3[CH:31]=[CH:32][C:33]([C@@H:37]([OH:101])[C@@H:38]([NH:91][C:92]([C@H:94]([NH:99][CH3:100])[CH2:95][CH:96]([CH3:98])[CH3:97])=[O:93])[C:39]([NH:41][C@@H:42]([CH2:87][C:88]([NH2:90])=[O:89])[C:43]([NH:45]5)=[O:44])=[O:40])=[CH:34][C:35]=3[Cl:36])[CH:25]=4)[O:20][C@H:19]([CH2:102][OH:103])[C@@H:18]([OH:104])[C@@H:17]2[OH:105])[CH2:12][C@@:11]([NH2:107])([CH3:106])[C@@H:10]1[OH:108].Cl.ON1C2C=CC=CC=2SC1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH3:8][C@@H:9]1[O:14][C@@H:13]([O:15][C@H:16]2[C@H:21]([O:22][C:23]3[C:24]4[O:78][C:74]5=[C:75]([Cl:77])[CH:76]=[C:71]([CH:72]=[CH:73]5)[C@@H:70]([OH:79])[C@@H:69]5[NH:80][C:81](=[O:82])[C@@H:50]([C:51]6[CH:52]=[CH:53][C:54]([OH:86])=[C:55]([C:57]7[C:62]([OH:63])=[CH:61][C:60]([OH:64])=[CH:59][C:58]=7[C@@H:65]([C:83]([OH:85])=[O:84])[NH:66][C:67]5=[O:68])[CH:56]=6)[NH:49][C:47](=[O:48])[C@H:46]5[C:26](=[CH:27][C:28]=3[O:29][C:30]3[CH:31]=[CH:32][C:33]([C@@H:37]([OH:101])[C@@H:38]([NH:91][C:92]([C@H:94]([NH:99][CH3:100])[CH2:95][CH:96]([CH3:97])[CH3:98])=[O:93])[C:39]([NH:41][C@@H:42]([CH2:87][C:88]([NH2:90])=[O:89])[C:43]([NH:45]5)=[O:44])=[O:40])=[CH:34][C:35]=3[Cl:36])[CH:25]=4)[O:20][C@H:19]([CH2:102][OH:103])[C@@H:18]([OH:104])[C@@H:17]2[OH:105])[CH2:12][C@@:11]([NH2:107])([CH3:106])[C@@H:10]1[OH:108]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 6420023Vancomycin monohydrochlorideHCID 15176256N-hydroxybenzothiazole

Product 1

HCID 14969Vancomycin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Triethylamine (2 mL) was added to a DMF solution (30 mL) containing vancomycin hydrochloride (1 g), biotinlyated amine (biotin-hexanediamine-aminocaproic acid, 0.4 g), and N-hydroxybenzothiazole (200 mg). After addition of 1,3-dicyclohexylcarbodiimide (1.48 g), the mixture was heated at 50° C. for 10 h and then left at ambient temperature for overnight. The solvent was evaporated to dryness. The residue was eluted on a silica gel column firstly using ethyl acetate:methanol:dichloromethane:ammonium hydroxide (6:6:2:1.2 by volume), and then 5-7% by volume of ammonium hydroxide in methanol. The ammonium-methanol fractions containing vancomycin bidentate was pooled, and the solvent was evaporated to give the solid vancomycin bidentate (yield: 0.16 g).

Workup

  1. customThe solvent was evaporated to dryness
  2. washThe residue was eluted on a silica gel column firstly using ethyl acetate:methanol:dichloromethane:ammonium hydroxide (6:6:2:1.2 by volume)
  3. additionThe ammonium-methanol fractions containing vancomycin bidentate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0602082d8bd340fe8e1ebfba263caed2
Source dataset
uspto-grants-2004_10
Patent number
US06800608B2

Reaction notes

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