Trifluoroacetic acid → Vancomycin
反応式
[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]参加物
9
反応条件
- 温度
- 0 °C
実験手順
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.
後処理
- 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
出典と根拠
- ORDレコード
- ord-5bbc90297be54818be30ce30bdce5999
- 出典データセット
- uspto-grants-2011_01
- 特許番号
- US07871997B2
反応ノート
読み込み中…