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

HRID 25733Notes

Reaction equation

HRID 25733 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@H:8]([N:14]2[CH:19]=[CH:18][C:17](=[O:20])[NH:16][C:15]2=[O:21])[O:7][C@@H:6]1[C@H:22]([OH:53])[CH:23]([C:48]([O:50][CH2:51][CH3:52])=[O:49])[NH:24][CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:47])[C@H:30]([C@@H:42]([OH:46])[CH:43]([CH3:45])[CH3:44])[NH:31]C(=O)OCC1C=CC=CC=1)(=[O:3])[CH3:2]>[Pd].CO>[NH2:31][C@@H:30]([C@@H:42]([OH:46])[CH:43]([CH3:45])[CH3:44])[C:29]([NH:28][CH2:27][CH2:26][CH2:25][NH:24][CH:23]([C@H:22]([C@@H:6]1[C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@H:8]([N:14]2[CH:19]=[CH:18][C:17](=[O:20])[NH:16][C:15]2=[O:21])[O:7]1)[OH:53])[C:48]([O:50][CH2:51][CH3:52])=[O:49])=[O:47]

Participants

4

Reactant 1

HCID 86587952ethyl (5S)-12-[(R)-[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl](hydroxy)methyl]-5-[(1S)-1-hydroxy-2-methylpropyl]-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate

Product 1

HCID 86587953ethyl (3R)-2-[(3-{[(2S,3S)-2-amino-3-hydroxy-4-methylpentanoyl]amino}propyl)amino]-3-[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]-3-hydroxypropanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl (5S)-12-[(R)-[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl](hydroxy)methyl]-5-[(1S)-1-hydroxy-2-methylpropyl]-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (obtained from Example 36) was hydrogenated using 10% palladium on carbon in absolute methanol under atmospheric pressure, to give ethyl (3R)-2-[(3-{[(2S,3S)-2-amino-3-hydroxy-4-methylpentanoyl]amino}propyl)amino]-3-[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]-3-hydroxypropanoate as a white amorphous solid [MS (ES) 616.1 (M+H)].

Sources & evidence

ORD record
ord-b5d80d67266e4399b1fb8467714e8a99
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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