HCID 59065879, compound → tert-butyl (2S,3R)-2-amino-3-[(2R,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]-3-hydroxy-propanoate

HRID 25680Notes

Reaction equation

HRID 25680 reaction equation
[C:1]([Si:5]([CH3:63])([CH3:62])[O:6][C@H:7]1[C@@H:11]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[C@H:10]([N:20]2[CH:25]=[CH:24][C:23](=[O:26])[N:22]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[C:21]2=[O:36])[O:9][C@@H:8]1[C@H:37]([OH:61])[C@H:38]([N:46](CC1C=CC=CC=1)CC1C=CC=CC=1)[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[NH2:46][C@@H:38]([C@H:37]([C@@H:8]1[C@@H:7]([O:6][Si:5]([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:63])[CH3:62])[C@@H:11]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15])[C@H:10]([N:20]2[CH:25]=[CH:24][C:23](=[O:26])[N:22]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[C:21]2=[O:36])[O:9]1)[OH:61])[C:39]([O:41][C:42]([CH3:44])([CH3:43])[CH3:45])=[O:40]

Participants

4

Reactant 1

HCID 59065879HCID 59065879, compound

Product 1

HCID 12137063tert-butyl (2S,3R)-2-amino-3-[(2R,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]-3-hydroxy-propanoateYield 25%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl (2S,3R)-3-[(2R,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-(dibenzylamino)-3-hydroxy-propanoate (3.0 g, 3.33 mmole, obtained from Reference Example 4) was hydrogenated using 10% palladium on carbon (2 g) in methanol (70 ml) under atmospheric pressure. The catalyst was removed, and the volatile was removed in vacuo. The residue was chromatographed (flash column, silica gel, methylene chloride:methanol:diethyl ether=92:4:4) to give the recovered starting material (1.2 g, 50%) and tert-butyl (2S,3R)-2-amino-3-[(2R,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]-3-hydroxypropanoate (600 mg, 25%) as a white amorphous solid.

Workup

  1. customThe catalyst was removed
  2. customthe volatile was removed in vacuo
  3. customThe residue was chromatographed (flash column, silica gel, methylene chloride:methanol:diethyl ether=92:4:4)

Sources & evidence

ORD record
ord-dd35e8e0003a4913aabe8af67c7ae413
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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