HCID 86632144, compound → HCID 86632143, compound

HRID 253757Notes

Reaction equation

HRID 253757 reaction equation
[OH:1][C@@H:2]([C@@H:4]1[NH:36][C:35](=[O:37])[C@H:34]([C@H:38]([OH:45])[C@H:39]([CH3:44])[CH2:40]/[CH:41]=[CH:42]/[CH3:43])[N:33]([CH3:46])[C:32](=[O:47])[C@H:31]([CH:48]([CH3:50])[CH3:49])[N:30]([CH3:51])[C:29](=[O:52])[C@H:28]([CH2:53][CH:54]([CH3:56])[CH3:55])[NH:27][C:26](=[O:57])[C@H:25]([CH2:58][CH:59]([CH3:61])[CH3:60])[N:24]([CH3:62])[C:23](=[O:63])[C@@H:22]([CH3:64])[NH:21][C:20](=[O:65])[C@H:19]([CH3:66])[NH:18][C:17](=[O:67])[C@H:16]([CH2:68][CH:69]([CH3:71])[CH3:70])[N:15]([CH3:72])[C:14](=[O:73])[C@H:13]([CH2:74][CH:75]([CH3:77])[CH3:76])[NH:12][C:11](=[O:78])[C@H:10]([CH:79]([O:81][CH3:82])[CH3:80])[N:9]([CH3:83])[C:8](=[O:84])[C@@H:7]([CH3:85])[N:6]([CH3:86])[C:5]1=[O:87])[CH3:3]>CO.[Pd]>[OH:1][C@@H:2]([C@@H:4]1[NH:36][C:35](=[O:37])[C@H:34]([C@H:38]([OH:45])[C@H:39]([CH3:44])[CH2:40][CH2:41][CH2:42][CH3:43])[N:33]([CH3:46])[C:32](=[O:47])[C@H:31]([CH:48]([CH3:49])[CH3:50])[N:30]([CH3:51])[C:29](=[O:52])[C@H:28]([CH2:53][CH:54]([CH3:55])[CH3:56])[NH:27][C:26](=[O:57])[C@H:25]([CH2:58][CH:59]([CH3:61])[CH3:60])[N:24]([CH3:62])[C:23](=[O:63])[C@@H:22]([CH3:64])[NH:21][C:20](=[O:65])[C@H:19]([CH3:66])[NH:18][C:17](=[O:67])[C@H:16]([CH2:68][CH:69]([CH3:70])[CH3:71])[N:15]([CH3:72])[C:14](=[O:73])[C@H:13]([CH2:74][CH:75]([CH3:77])[CH3:76])[NH:12][C:11](=[O:78])[C@H:10]([CH:79]([O:81][CH3:82])[CH3:80])[N:9]([CH3:83])[C:8](=[O:84])[C@@H:7]([CH3:85])[N:6]([CH3:86])[C:5]1=[O:87])[CH3:3]

Participants

4

Reactant 1

HCID 86632144HCID 86632144, compound

Product 1

HCID 86632143HCID 86632143, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (3R,6S,9S,12S,15S,18S,21R,24S,27S,30S,33S)-6-[(1R)-1-hydroxyethyl]-9-[(1R,2R,4E)-1-hydroxy-2-methylhex-4-en-1-yl]-15,18,27,30-tetraisobutyl-12-isopropyl-33-(1-methoxyethyl)-1,3,4,10,13,19,21,24,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone (60 mg) in MeOH (6.0 ml) was hydrogenated over 20% Pd/C (50% wet; 30 mg) at room temperature for 2 hrs. The mixture was filtered and the filtrate was concentrated. The residue was evaporated to give (3R,6S,9S,12S,15S,18S,21R,24S,27S,30S,33S)-6-[(1R)-1-hydroxyethyl]-9-[(1R,2R)-1-hydroxy-2-methylhexyl]-15,18,27,30-tetraisobutyl-12-isopropyl-33-(1-methoxyethyl)-1,3,4,10,13,19,21,24,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone (56 mg).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was evaporated

Sources & evidence

ORD record
ord-413c78ed9f1741d28c542192a4c34a9a
Source dataset
uspto-grants-2011_01
Patent number
US07872097B2

Reaction notes

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