Morpholine → HCID 131736698, compound

HRID 1482273Notes

Reaction equation

N1CCOCC1.[C:7]([S:11][S:12][CH2:13][C@H:14]([NH:101]C(=O)OCC=C)[C:15](=[O:100])[NH:16][CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]1[C:50](=[O:51])[N:49]([CH3:52])[C@@H:48]([CH2:53][CH:54]([CH3:56])[CH3:55])[C:47](=[O:57])[NH:46][C@@H:45]([CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[C:44](=[O:65])[N:43]([CH3:66])[CH2:42][C:41](=[O:67])[N:40]([CH3:68])[C@@H:39]([CH2:69][C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)[C:38](=[O:76])[NH:37][C@@H:36]([CH3:77])[C:35](=[O:78])[N:34]([CH3:79])[C@@H:33]([CH3:80])[C:32](=[O:81])[NH:31][C@@H:30]([CH2:82][C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)[C:29](=[O:89])[O:28][CH2:27][C:26](=[O:90])[N:25]([CH3:91])[C@@H:24]([CH2:92][C:93]2[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=2)[C:23](=[O:99])[NH:22]1)([CH3:10])([CH3:9])[CH3:8]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:101][C@@H:14]([CH2:13][S:12][S:11][C:7]([CH3:10])([CH3:8])[CH3:9])[C:15]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]1[C:50](=[O:51])[N:49]([CH3:52])[C@@H:48]([CH2:53][CH:54]([CH3:56])[CH3:55])[C:47](=[O:57])[NH:46][C@@H:45]([CH2:58][C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=2)[C:44](=[O:65])[N:43]([CH3:66])[CH2:42][C:41](=[O:67])[N:40]([CH3:68])[C@@H:39]([CH2:69][C:70]2[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=2)[C:38](=[O:76])[NH:37][C@@H:36]([CH3:77])[C:35](=[O:78])[N:34]([CH3:79])[C@@H:33]([CH3:80])[C:32](=[O:81])[NH:31][C@@H:30]([CH2:82][C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)[C:29](=[O:89])[O:28][CH2:27][C:26](=[O:90])[N:25]([CH3:91])[C@@H:24]([CH2:92][C:93]2[CH:94]=[CH:95][CH:96]=[CH:97][CH:98]=2)[C:23](=[O:99])[NH:22]1)=[O:100]

Participants

Conditions

Temperature: 30 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (2.0 mg, 0.002 mmol) and morpholine (5.62 ml, 0.064 mmol) were added to a solution of allyl (R)-3-(tert-butyldisulfanyl)-1-oxo-1-(4-((5S,8S,11S,14S,20S,23S,26S,29S)-5,14,20,29-tetrabenzyl-11-isobutyl-4,10,16,19,23,25,26-heptamethyl-3,6,9,12,15,18,21,24,27,30-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclotriacontan-8-yl)butylamino)propan-2-ylcarbamate (Compound 150b) (23.1 mg, 0.016 mmol) in THF (0.16 ml) under a nitrogen atmosphere, and the reaction solution was stirred at 30° C. for 4 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by reverse-phase silica gel column chromatography (0.1% aqueous formic acid solution/0.1% formic acid-acetonitrile solution) to afford the title compound P-150 (10.2 mg, 47%).

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customthe resulting residue was purified by reverse-phase silica gel column chromatography (0.1% aqueous formic acid solution/0.1% formic acid-acetonitrile solution)

Sources & evidence

ORD record: ord-78ed18998dfc46d4adeda4d2800bb0d1
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409952B2

Reaction notes

Loading…