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-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate → tert-butyl (2S,3R)-2-[(3-{[(2S)-2-amino-4-methylpentanoyl]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

HRID 25741Notes

Reaction equation

HRID 25741 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:57])[C@@H:26]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[NH:27][CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:49])[C@H:33]([CH2:45][CH:46]([CH3:48])[CH3:47])[NH:34]C(=O)OCC1C=CC=CC=1>CO.[Pd]>[NH2:34][C@@H:33]([CH2:45][CH:46]([CH3:48])[CH3:47])[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:57])[C:50]([O:52][C:53]([CH3:54])([CH3:56])[CH3:55])=[O:51])=[O:49]

Participants

4

Reactant 1

HCID 59065928tert-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-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate

Product 1

HCID 10233418tert-butyl (2S,3R)-2-[(3-{[(2S)-2-amino-4-methylpentanoyl]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-hydroxypropanoateYield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

By using an analogous procedure to that described for Example 45, 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-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (20 mg, 0.025 mmol, obtained from Example 51) was hydrogenated in methanol (1 ml) using 10% palladium on carbon (8 mg) for 4 hours to provide tert-butyl (2S,3R)-2-[(3-{[(2S)-2-amino-4-methylpentanoyl]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 (15 mg, 90%) as a white solid.

Workup

  1. customfor 4 hours

Sources & evidence

ORD record
ord-71fd4d6fa39b4cd18a4f9a6d9153cf35
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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