HCID 59065917, compound → tert-butyl (2S,3R)-2-[(3-{[(2S)-2-aminopropanoyl]amino}propyl)amino]-3-[(3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]-3-hydroxypropanoate

HRID 25721Notes

Reaction equation

HRID 25721 reaction equation
[Si:1]([O:8][C@H:9]1[C@@H:13]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C@H:12]([N:22]2[CH:27]=[CH:26][C:25](=[O:28])[N:24]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[C:23]2=[O:38])[O:11][CH:10]1[C@H:39]([OH:68])[C@@H:40]([C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[NH:41][CH2:42][CH2:43][CH2:44][NH:45][C:46](=[O:60])[C@H:47]([CH3:59])[NH:48]C(=O)OCC1C=CC=CC=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:48][C@@H:47]([CH3:59])[C:46]([NH:45][CH2:44][CH2:43][CH2:42][NH:41][C@@H:40]([C@H:39]([CH:10]1[C@@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[C@@H:13]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:16])[CH3:17])[C@H:12]([N:22]2[CH:27]=[CH:26][C:25](=[O:28])[N:24]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[C:23]2=[O:38])[O:11]1)[OH:68])[C:61]([O:63][C:64]([CH3:66])([CH3:67])[CH3:65])=[O:62])=[O:60]

Participants

4

Reactant 1

HCID 59065917HCID 59065917, compound

Product 1

HCID 10284318tert-butyl (2S,3R)-2-[(3-{[(2S)-2-aminopropanoyl]amino}propyl)amino]-3-[(3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]-3-hydroxypropanoateYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

By using an analogous procedure to that described in Example 2, tert-butyl (5S,12S)-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl](hydroxy)methyl]-5-methyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (43 mg, 0.044 mmol, obtained from Example 14) was hydrogenated in methanol (1.5 ml) using 10% palladium on carbon (10 mg) to provide tert-butyl (2S,3R)-2-[(3-{[(2S)-2-aminopropanoyl]amino}propyl)amino]-3-[(3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]-3-hydroxypropanoate (35 mg, 94%) as a white amorphous solid.

Sources & evidence

ORD record
ord-959a0ef24d78490988b23eae625899e7
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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