HCID 136352424, compound → HCID 136184175, compound

HRID 1794623Notes

Reaction equation

[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:37](=[O:38])[O:36][CH2:35][C:28]3[CH:29]=[CH:30][CH:31]=[C:32]4[N:33]([OH:34])[C:25]5=[C:26]([CH2:39][O:40][C@H:10]2[C@@H:11]2[NH:85][C:83](=[O:84])[C:80]6=[CH:81][S:82][C:78](=[N:79]6)/[C:73](=[C:74](\[O:76][CH3:77])/[CH3:75])/[NH:72][C:70](=[O:71])[C@H:69]([C@H:86]([OH:88])[CH3:87])[NH:68][C:66](=[O:67])[C:63]6=[CH:64][S:65][C:61](=[N:62]6)[C:47]6[CH:48]=[C:49]([OH:60])[C:50]([C:52]7[S:56][CH:55]=[C:54]([C:57]([NH2:59])=[O:58])[N:53]=7)=[N:51][C:46]=6[C:43]6=[CH:44][S:45][C:41](=[N:42]6)[C@H:20]([CH2:21][O:22][C:23]5=[O:24])[NH:19][C:17](=[O:18])[C:14]5=[CH:15][S:16][C:12]2=[N:13]5)[C:27]=34)[CH2:5][C@@:4]([OH:90])([CH3:89])[C@@H:3]1[N:91]([CH3:93])[CH3:92].C(O)(C(F)(F)F)=O>C1COCC1.CC#N>[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:37](=[O:38])[O:36][CH2:35][C:28]3[CH:29]=[CH:30][CH:31]=[C:32]4[N:33]([OH:34])[C:25]5=[C:26]([CH2:39][O:40][C@H:10]2[C@@H:11]2[NH:85][C:83](=[O:84])[C:80]6=[CH:81][S:82][C:78](=[N:79]6)/[C:73](=[C:74](\[O:76][CH3:77])/[CH3:75])/[NH:72][C:70](=[O:71])[C@H:69]([C@H:86]([OH:88])[CH3:87])[NH:68][C:66](=[O:67])[C:63]6=[CH:64][S:65][C:61](=[N:62]6)[C:47]6[CH:48]=[C:49]([OH:60])[C:50]([C:52]7[S:56][CH:55]=[C:54]([C:57]([NH2:59])=[O:58])[N:53]=7)=[N:51][C:46]=6[C:43]6=[CH:44][S:45][C:41](=[N:42]6)[C@H:20]([CH2:21][O:22][C:23]5=[O:24])[NH:19][C:17](=[O:18])[C:14]5=[CH:15][S:16][C:12]2=[N:13]5)[C:27]=34)[CH2:5][C@@:4]([OH:90])([CH3:89])[C@@H:3]1[N:91]([CH3:93])[CH3:92]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of nocathiacin IV-TFA salt (compound of Preparation 2, 35 mg) in THF/CH3CN (3.5 mL, 6:1) was added 1,3-2-diazaphosphorine on polystyrene (26 mg, 2.3 mmol/g) and the mixture was stirred at 25° C. for 30 minutes. The resin-bound base (1,3-2-diazaphosphorine on polystyrene) was then removed by filtration. The filter cake was washed with MeOH, THF, CH3CN and H2O. The filtrate was then concentrated under reduced pressure in order to remove volatiles. The resulting solution was frozen and lyophilized to afford 24 mg of nocathiacin IV as the free base.

Workup

customThe resin-bound base (1,3-2-diazaphosphorine on polystyrene) was then removed by filtration
washThe filter cake was washed with MeOH, THF, CH3CN and H2O
concentrationThe filtrate was then concentrated under reduced pressure in order
customto remove volatiles
temperatureThe resulting solution was frozen

Sources & evidence

ORD record: ord-9ab780eb40974e819dd3380d87167e78
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022667B2

Reaction notes

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