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-hydroxyethyl]-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate → ethyl (3R)-2-[(3-{[(2S,3S)-2-amino-3-hydroxybutanoyl]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 25731Notes

Reaction equation

HRID 25731 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:51])[CH:23]([C:46]([O:48][CH2:49][CH3:50])=[O:47])[NH:24][CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:45])[C@H:30]([C@@H:42]([OH:44])[CH3:43])[NH:31]C(=O)OCC1C=CC=CC=1)(=[O:3])[CH3:2]>[Pd].CO>[NH2:31][C@@H:30]([C@@H:42]([OH:44])[CH3:43])[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:51])[C:46]([O:48][CH2:49][CH3:50])=[O:47])=[O:45]

Participants

4

Reactant 1

HCID 86587951Ethyl (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-hydroxyethyl]-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate

Product 1

HCID 86587950ethyl (3R)-2-[(3-{[(2S,3S)-2-amino-3-hydroxybutanoyl]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-hydroxypropanoateYield 94.4%

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-hydroxyethyl]-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (86 mg, 0.119 mmole, obtained from Example 31) was hydrogenated using 10% palladium on carbon in methanol (2 ml) under atmospheric pressure. The catalyst was removed and the volatiles were removed in vacuo to provide ethyl (3R)-2-[(3-{[(2S,3S)-2-amino-3-hydroxybutanoyl]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 (66 mg, 94%) as a white amorphous solid.

Workup

  1. customThe catalyst was removed
  2. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-e547c2d076f6416fa5e314ab2367c633
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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