tert-Butyl (2S,3S)-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 → HCID 59065916, compound

HRID 25679

Reaction equation

HRID 25679 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 59065932tert-Butyl (2S,3S)-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

Product 1

HCID 59065916HCID 59065916, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl (2S,3S)-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 (850 mg, 0.942 mmole, obtained from Reference Example 4) was hydrogenated using 10% palladium on carbon in methanol (10 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=95:2:3) to give the recovered starting material (248 mg, 29%) and tert-butyl (2S,3S)-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 (141 mg, 21%) 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=95:2:3)

Sources & evidence

ORD record
ord-5da621dc1348407c9ac832980e18e9e3
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Linked notes

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