ethyl (5S)-12-{(R)-(acetyloxy)[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]methyl}-5-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate → ethyl (3R)-3-(acetyloxy)-2-[(3-{[(2S)-2-amino-4-methylpentanoyl]amino}propyl)amino]-3-[(2R,3R,4R,5S)-3,4-bis(acetyloxy)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]propanoate

HRID 25734Notes

Reaction equation

HRID 25734 reaction equation
[C:1]([O:4][C@@H:5]([C@@H:35]1[C@@H:39]([O:40][C:41](=[O:43])[CH3:42])[C@@H:38]([O:44][C:45](=[O:47])[CH3:46])[C@H:37]([N:48]2[CH:53]=[CH:52][C:51](=[O:54])[NH:50][C:49]2=[O:55])[O:36]1)[CH:6]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:29])[C@H:13]([CH2:25][CH:26]([CH3:28])[CH3:27])[NH:14]C(=O)OCC1C=CC=CC=1)(=[O:3])[CH3:2]>[Pd].CO>[C:1]([O:4][C@@H:5]([C@@H:35]1[C@@H:39]([O:40][C:41](=[O:43])[CH3:42])[C@@H:38]([O:44][C:45](=[O:47])[CH3:46])[C@@H:37]([N:48]2[CH:53]=[CH:52][C:51](=[O:54])[NH:50][C:49]2=[O:55])[O:36]1)[CH:6]([NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:29])[C@@H:13]([NH2:14])[CH2:25][CH:26]([CH3:27])[CH3:28])[C:30]([O:32][CH2:33][CH3:34])=[O:31])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86587955ethyl (5S)-12-{(R)-(acetyloxy)[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]methyl}-5-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate

Product 1

HCID 86587954ethyl (3R)-3-(acetyloxy)-2-[(3-{[(2S)-2-amino-4-methylpentanoyl]amino}propyl)amino]-3-[(2R,3R,4R,5S)-3,4-bis(acetyloxy)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]propanoateYield 103.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl (5S)-12-[(R)-(acetyloxy)[(2R,3R,4R,5S)-3,4-bis(acetyloxy)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]methyl}-5-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-1-oate (88 mg, 0.114 mmole, obtained from Example 38) was hydrogenated using 10% palladium on carbon in methanol (2 ml) under atmospheric pressure to provide ethyl (3R)-3-(acetyloxy)-2-[(3-{[(2S)-2-amino-4-methylpentanoyl]amino}propyl)amino]-3-[(2R,3R,4R,5S)-3,4-bis(acetyloxy)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]propanoate (76 mg, 95%) as a white glassy solid.

Sources & evidence

ORD record
ord-c752c04b742c46e09d114f7cb56a43a2
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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