HCID 86587957, compound → HCID 86587958, compound

HRID 25737Notes

Reaction equation

HRID 25737 reaction equation
[OH:1][C@H:2]1[C@@H:6]([OH:7])[C@H:5]([N:8]2[CH:13]=[CH:12][C:11](=[O:14])[N:10]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:9]2=[O:24])[O:4][CH:3]1[C@H:25]([OH:56])[C@@H:26]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[NH:27][CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:48])[C@H:33]([C@@H:45]([OH:47])[CH3:46])[NH:34]C(=O)OCC1C=CC=CC=1>CO.[Pd]>[NH2:34][C@@H:33]([C@@H:45]([OH:47])[CH3:46])[C:32]([NH:31][CH2:30][CH2:29][CH2:28][NH:27][C@@H:26]([C@H:25]([CH:3]1[C@@H:2]([OH:1])[C@@H:6]([OH:7])[C@H:5]([N:8]2[CH:13]=[CH:12][C:11](=[O:14])[N:10]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:9]2=[O:24])[O:4]1)[OH:56])[C:49]([O:51][C:52]([CH3:53])([CH3:54])[CH3:55])=[O:50])=[O:48]

Participants

4

Reactant 1

HCID 86587957HCID 86587957, compound

Product 1

HCID 86587958HCID 86587958, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl (5S,12S)-12-[(R)-[(3S,4R,5R)-3,4-dihydroxy-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]-(hydroxy)methyl]-5-[(1S)-1-hydroxyethyl]-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (8 mg, 0.01 mmol, obtained from Example 44) was hydrogenated in methanol (2 ml) using 10% palladium on carbon (5 mg) under atmospheric pressure for 4 hours. The catalyst was removed and the volatiles was concentrated in vacuo to provide tert-butyl (2S,3R)-2-[(3-{[(2S,3S)-2-amino-3-hydroxybutanoyl]amino}propyl)amino]-3-[(3S,4R,5R)-3,4-dihydroxy-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-tetrahydro-2-furanyl]-3-hydroxypropanoate (6 mg, 92%) as a yellow solid.

Workup

  1. customfor 4 hours
  2. customThe catalyst was removed
  3. concentrationthe volatiles was concentrated in vacuo

Sources & evidence

ORD record
ord-90f63e1176a9402ba0a0469591e8be17
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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