HCID 70001049, compound → HCID 59032968, compound

HRID 1634844Notes

Reaction equation

HRID 1634844 reaction equation
C([O:8][C:9](=[O:54])[C@H:10]([NH:22][C:23](=[O:53])[C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][CH:33]([CH2:36][NH:37][CH2:38][C@H:39]([OH:52])[C:40]3[CH:45]=[CH:44][C:43]([OH:46])=[C:42]([NH:47][S:48]([CH3:51])(=[O:50])=[O:49])[CH:41]=3)[CH2:32][CH2:31]2)=[CH:26][CH:25]=1)[CH2:11][C:12]([O:14]CC1C=CC=CC=1)=[O:13])C1C=CC=CC=1>[Pd].C(O)C.C1CCCCC=1>[OH:52][C@H:39]([C:40]1[CH:45]=[CH:44][C:43]([OH:46])=[C:42]([NH:47][S:48]([CH3:51])(=[O:49])=[O:50])[CH:41]=1)[CH2:38][NH:37][CH2:36][CH:33]1[CH2:32][CH2:31][N:30]([C:27]2[CH:28]=[CH:29][C:24]([C:23]([NH:22][C@H:10]([CH2:11][C:12]([OH:14])=[O:13])[C:9]([OH:54])=[O:8])=[O:53])=[CH:25][CH:26]=2)[CH2:35][CH2:34]1

Participants

5

Reactant 1

HCID 70001049HCID 70001049, compound

Product 1

HCID 59032968HCID 59032968, compoundYield 12.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8079CyclohexeneSolvent

Procedure

A mixture of (2R)-2-{[4-(4-({[(2R)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)-amino]-phenyl}ethyl)amino]methyl}piperidin-1-yl)benzoyl]-amino}butanedioic acid dibenzyl ester (0.110 g, 0.14 mmol) and 0.11 g of 10% palladium on carbon in ethanol (3 mL) and cyclohexene (1 mL) was heated at reflux for 3 hours. When complete, the catalyst was filtered (Celite) and the cake was washed with hot methanol. The solvent was removed under reduced pressure, to give the title compound (0.010 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. filtrationWhen complete, the catalyst was filtered (Celite)
  4. washthe cake was washed with hot methanol
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4236636614ab4a9793c89e7af474be9f
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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