Trifluoroacetic acid → Vancomycin

HRID 253050Notizen

Reaktionsgleichung

[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([O:15][C:16]3[C:17]4[O:71][C:67]5=[C:68]([Cl:70])[CH:69]=[C:64]([CH:65]=[CH:66]5)[C@@H:63]([OH:72])[C@@H:62]5[NH:73][C:74](=[O:75])[C@@H:43]([C:44]6[CH:45]=[CH:46][C:47]([OH:79])=[C:48]([C:50]7[C:55]([OH:56])=[CH:54][C:53]([OH:57])=[CH:52][C:51]=7[C@@H:58]([C:76]([OH:78])=[O:77])[NH:59][C:60]5=[O:61])[CH:49]=6)[NH:42][C:40](=[O:41])[C@H:39]5[C:19](=[CH:20][C:21]=3[O:22][C:23]3[CH:24]=[CH:25][C:26]([C@@H:30]([OH:94])[C@@H:31]([NH:84][C:85]([C@H:87]([NH:92][CH3:93])[CH2:88][CH:89]([CH3:91])[CH3:90])=[O:86])[C:32]([NH:34][C@@H:35]([CH2:80][C:81]([NH2:83])=[O:82])[C:36]([NH:38]5)=[O:37])=[O:33])=[CH:27][C:28]=3[Cl:29])[CH:18]=4)[O:13][C@H:12]([CH2:95][OH:96])[C@@H:11]([OH:97])[C@@H:10]2[OH:98])[CH2:5][C@@:4]([NH2:100])([CH3:99])[C@@H:3]1[OH:101].Cl.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(O)(C(F)(F)F)=O.N1C(C)=CC(C)=CC=1C>CS(C)=O.CN(C=O)C>[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([O:15][C:16]3[C:17]4[O:71][C:67]5=[C:68]([Cl:70])[CH:69]=[C:64]([CH:65]=[CH:66]5)[C@@H:63]([OH:72])[C@@H:62]5[NH:73][C:74](=[O:75])[C@@H:43]([C:44]6[CH:45]=[CH:46][C:47]([OH:79])=[C:48]([C:50]7[C:55]([OH:56])=[CH:54][C:53]([OH:57])=[CH:52][C:51]=7[C@@H:58]([C:76]([OH:78])=[O:77])[NH:59][C:60]5=[O:61])[CH:49]=6)[NH:42][C:40](=[O:41])[C@H:39]5[C:19](=[CH:20][C:21]=3[O:22][C:23]3[CH:24]=[CH:25][C:26]([C@@H:30]([OH:94])[C@@H:31]([NH:84][C:85]([C@H:87]([NH:92][CH3:93])[CH2:88][CH:89]([CH3:90])[CH3:91])=[O:86])[C:32]([NH:34][C@@H:35]([CH2:80][C:81]([NH2:83])=[O:82])[C:36]([NH:38]5)=[O:37])=[O:33])=[CH:27][C:28]=3[Cl:29])[CH:18]=4)[O:13][C@H:12]([CH2:95][OH:96])[C@@H:11]([OH:97])[C@@H:10]2[OH:98])[CH2:5][C@@:4]([NH2:100])([CH3:99])[C@@H:3]1[OH:101]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Vancomycin hydrochloride, 1a (0.32 g, 0.21 mmol), was dissolved in 3 mL of DMSO. A 0.5 mL solution of PyBOP (0.11 g, 0.21 mmol) and HOAT (0.03 g, 0.21 mmol) in DMF was added, followed by DIPEA (0.04 mL, 0.21 mmol). The reaction was stirred 30 minutes, then TFA (0.02 mL, 0.21 mmol) was added, and the mixture was cooled to 0° C. A solution of 3b (0.15 g, 0.17 mmol) (see FIG. 6) in DMF (1 mL) was then added, followed by collidine (0.08 mL, 0.63 mmol). The reaction was stirred at 4° C. overnight and then precipitated from EtOAc, centrifuged and the resulting solid washed with MeCN. The desired compound was purified by HPLC (2-30% MeCN) to give 0.3 g of Ie as a white solid.

Aufarbeitung

stirringThe reaction was stirred at 4° C. overnight
customprecipitated from EtOAc
washcentrifuged and the resulting solid washed with MeCN
customThe desired compound was purified by HPLC (2-30% MeCN)
customto give 0.3 g of Ie as a white solid

Quellen und Nachweise

ORD-Eintrag: ord-5bbc90297be54818be30ce30bdce5999
Quelldatensatz: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07871997B2

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