HCID 59065905, compound → (3S)-3-amino-4-[(3-{[(1S,2S)-2-[(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]-1-(tert-butoxycarbonyl)-2-hydroxyethyl]amino}propyl)amino]-4-oxobutanoic acid

HRID 25723Notes

Reaction equation

HRID 25723 reaction equation
C([O:8][C:9](=[O:78])[CH2:10][C@@H:11]([C:23](=[O:77])[NH:24][CH2:25][CH2:26][CH2:27][NH:28][C@@H:29]([C@H:37]([CH:39]1[C@@H:43]([O:44][Si:45]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46])[C@@H:42]([O:52][Si:53]([C:56]([CH3:59])([CH3:58])[CH3:57])([CH3:55])[CH3:54])[C@H:41]([N:60]2[CH:65]=[CH:64][C:63](=[O:66])[N:62]([CH2:67][C:68]3[CH:73]=[CH:72][C:71]([O:74][CH3:75])=[CH:70][CH:69]=3)[C:61]2=[O:76])[O:40]1)[OH:38])[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[NH:12]C(=O)OCC1C=CC=CC=1)C1C=CC=CC=1>CO.[Pd]>[NH2:12][C@H:11]([C:23]([NH:24][CH2:25][CH2:26][CH2:27][NH:28][C@H:29]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@@H:37]([CH:39]1[C@@H:43]([O:44][Si:45]([C:48]([CH3:51])([CH3:49])[CH3:50])([CH3:47])[CH3:46])[C@@H:42]([O:52][Si:53]([C:56]([CH3:59])([CH3:58])[CH3:57])([CH3:55])[CH3:54])[C@H:41]([N:60]2[CH:65]=[CH:64][C:63](=[O:66])[N:62]([CH2:67][C:68]3[CH:73]=[CH:72][C:71]([O:74][CH3:75])=[CH:70][CH:69]=3)[C:61]2=[O:76])[O:40]1)[OH:38])=[O:77])[CH2:10][C:9]([OH:78])=[O:8]

Participants

4

Reactant 1

HCID 59065905HCID 59065905, compound

Product 1

HCID 69754055(3S)-3-amino-4-[(3-{[(1S,2S)-2-[(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]-1-(tert-butoxycarbonyl)-2-hydroxyethyl]amino}propyl)amino]-4-oxobutanoic acidYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

By using an analogous procedure to that described for Example 2, tert-butyl (5S,12S)-5-[2-(benzyloxy)-2-oxoethyl]-12-[(R)-[(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](hydroxy)methyl]-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (20 mg, 0.018 mmol, obtained from Example 16) was hydrogenated in methanol (1.5 ml) using 10% palladium on carbon (10 mg) to provide (3S)-3-amino-4-[(3-{[(1S,2S)-2-[(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]-1-(tert-butoxycarbonyl)-2-hydroxyethyl]amino}propyl)amino]-4-oxobutanoic acid (16 mg, 99%) as a white solid.

Sources & evidence

ORD record
ord-0d67aaf0d26f4161afac6462400413c4
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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