HCID 86632142, compound → HCID 86632141, compound

HRID 253756Notes

Reaction equation

HRID 253756 reaction equation
C([O:8][CH2:9][C@H:10]1[N:42]([CH3:43])[C:41](=[O:44])[C@H:40]([C@H:45]([OH:47])[CH3:46])[NH:39][C:38](=[O:48])[C@H:37]([C@H:49]([OH:56])[C@H:50]([CH3:55])[CH2:51][CH2:52][CH2:53][CH3:54])[N:36]([CH3:57])[C:35](=[O:58])[C@H:34]([CH:59]([CH3:61])[CH3:60])[N:33]([CH3:62])[C:32](=[O:63])[C@H:31]([CH2:64][CH:65]([CH3:67])[CH3:66])[NH:30][C:29](=[O:68])[C@H:28]([CH2:69][CH:70]([CH3:72])[CH3:71])[N:27]([CH3:73])[C:26](=[O:74])[C@@H:25]([CH3:75])[NH:24][C:23](=[O:76])[C@H:22]([CH3:77])[NH:21][C:20](=[O:78])[C@H:19]([CH2:79][CH:80]([CH3:82])[CH3:81])[N:18]([CH3:83])[C:17](=[O:84])[C@H:16]([CH2:85][CH:86]([CH3:88])[CH3:87])[NH:15][C:14](=[O:89])[C@H:13]([CH2:90][CH:91]([CH3:93])[CH3:92])[N:12]([CH3:94])[C:11]1=[O:95])C1C=CC=CC=1>CO.[Pd]>[OH:47][C@@H:45]([C@@H:40]1[NH:39][C:38](=[O:48])[C@H:37]([C@H:49]([OH:56])[C@H:50]([CH3:55])[CH2:51][CH2:52][CH2:53][CH3:54])[N:36]([CH3:57])[C:35](=[O:58])[C@H:34]([CH:59]([CH3:60])[CH3:61])[N:33]([CH3:62])[C:32](=[O:63])[C@H:31]([CH2:64][CH:65]([CH3:67])[CH3:66])[NH:30][C:29](=[O:68])[C@H:28]([CH2:69][CH:70]([CH3:71])[CH3:72])[N:27]([CH3:73])[C:26](=[O:74])[C@@H:25]([CH3:75])[NH:24][C:23](=[O:76])[C@H:22]([CH3:77])[NH:21][C:20](=[O:78])[C@H:19]([CH2:79][CH:80]([CH3:81])[CH3:82])[N:18]([CH3:83])[C:17](=[O:84])[C@H:16]([CH2:85][CH:86]([CH3:88])[CH3:87])[NH:15][C:14](=[O:89])[C@H:13]([CH2:90][CH:91]([CH3:93])[CH3:92])[N:12]([CH3:94])[C:11](=[O:95])[C@@H:10]([CH2:9][OH:8])[N:42]([CH3:43])[C:41]1=[O:44])[CH3:46]

Participants

4

Reactant 1

HCID 86632142HCID 86632142, compound

Product 1

HCID 86632141HCID 86632141, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(3R,6S,9S,12S,15S,18S,21R,24S,27S,30S,33S)-3-[(Benzyloxy)methyl]-6-[(1R)-1-hydroxyethyl]-9-[(1R,2R)-1-hydroxy-2-methylhexyl]-15,18,27,30,33-pentaisobutyl-12-isopropyl-1,4,10,13,19,21,24,28-octamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone (22 mg) are dissolved in MeOH (1 ml) and hydrogenated at room temperature and atmospheric pressure over 5% Pd on charcoal. After 2 hrs, the catalyst was filtered off and the filtrate was concentrated in vacuo under reduced pressure. The residue was purified by silica-gel column chromatography (hexane-acetone, 1:1) to yield (3R,6S,9S,12S,15S,18S,21R,24S,27S,30S,33S)-6-[(1R)-1-hydroxyethyl]-3-(hydroxymethyl)-9-[(1R,2R)-1-hydroxy-2-methylhexyl]-15,18,27,30,33-pentaisobutyl-12-isopropyl-1,4,10,13,19,21,24,28-octamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone (18 mg).

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo under reduced pressure
  3. customThe residue was purified by silica-gel column chromatography (hexane-acetone, 1:1)

Sources & evidence

ORD record
ord-441c95e5022f48f8b0c17b770a127708
Source dataset
uspto-grants-2011_01
Patent number
US07872097B2

Reaction notes

Loading…