HCID 59065929, compound → tert-butyl (2S,3R)-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]-2-[(3-{[(2S)-2,6-diaminohexanoyl]amino}propyl) amino]-3-hydroxypropanoate

HRID 25724Notes

Reaction equation

HRID 25724 reaction equation
C(OC([NH:11][C@H:12]([C:28](=[O:82])[NH:29][CH2:30][CH2:31][CH2:32][NH:33][C@@H:34]([C@H:42]([CH:44]1[C@@H:48]([O:49][Si:50]([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:52])[CH3:51])[C@@H:47]([O:57][Si:58]([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59])[C@H:46]([N:65]2[CH:70]=[CH:69][C:68](=[O:71])[N:67]([CH2:72][C:73]3[CH:78]=[CH:77][C:76]([O:79][CH3:80])=[CH:75][CH:74]=3)[C:66]2=[O:81])[O:45]1)[OH:43])[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17]C(=O)OCC1C=CC=CC=1)=O)C1C=CC=CC=1>CO.[Pd]>[Si:50]([O:49][C@H:48]1[C@@H:47]([O:57][Si:58]([C:61]([CH3:64])([CH3:62])[CH3:63])([CH3:60])[CH3:59])[C@H:46]([N:65]2[CH:70]=[CH:69][C:68](=[O:71])[N:67]([CH2:72][C:73]3[CH:74]=[CH:75][C:76]([O:79][CH3:80])=[CH:77][CH:78]=3)[C:66]2=[O:81])[O:45][CH:44]1[C@H:42]([OH:43])[C@H:34]([NH:33][CH2:32][CH2:31][CH2:30][NH:29][C:28](=[O:82])[C@@H:12]([NH2:11])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])([C:53]([CH3:54])([CH3:55])[CH3:56])([CH3:51])[CH3:52]

Participants

4

Reactant 1

HCID 59065929HCID 59065929, compound

Product 1

HCID 10147694tert-butyl (2S,3R)-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]-2-[(3-{[(2S)-2,6-diaminohexanoyl]amino}propyl) amino]-3-hydroxypropanoateYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

By using an analogous procedure to that described for Example 2, tert-butyl (9S,16S)-9-{[(benzyloxy)carbonyl]amino}-16-[(R)-[(3R,4R,5R)-3,4-bis{[tert-pyrimidinyl)tetrahydro-2-furanyl](hydroxy)methyl]-3,10-dioxo-1-phenyl-2-oxa-4,11,15-triazaheptadecan-17-oate (70 mg, 0.06 mmol, obtained from Example 18) was hydrogenated in methanol (2 ml) using 10% palladium on carbon (17 mg) to provide tert-butyl (2S,3R)-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]-2-[(3-{[(2S)-2,6-diaminohexanoyl]amino}propyl) amino]-3-hydroxypropanoate (50 mg, 92%) as a white solid.

Sources & evidence

ORD record
ord-ea92cbac36194f8fa157da3da52a3cfe
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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