Trifluoroacetic acid → Vancomycin
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[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]참가 물질
9
반응 조건
- 온도
- 0 °C
실험 절차
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.
후처리
- 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
출처 및 근거
- ORD 기록
- ord-5bbc90297be54818be30ce30bdce5999
- 출처 데이터셋
- uspto-grants-2011_01
- 특허 번호
- US07871997B2
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