Sodium Carbonate → [(5S)-3-(5-{2-Fluoro-4-[(5R)-2-oxo-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]phenyl}pyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methyl beta-D-glucopyranoside

HRID 459057Notes

Reaction equation

HRID 459057 reaction equation
[O:1]([CH2:13][C@H:14]1[O:18][N:17]=[C:16]([C:19]2[CH:24]=[CH:23][C:22](Br)=[CH:21][N:20]=2)[CH2:15]1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[F:26][C:27]1[CH:28]=[C:29]([N:42]2[CH2:46][C@H:45]([CH2:47][N:48]3[CH:52]=[CH:51][N:50]=[N:49]3)[O:44][C:43]2=[O:53])[CH:30]=[CH:31][C:32]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:1]([CH2:13][C@H:14]1[O:18][N:17]=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:32]3[CH:31]=[CH:30][C:29]([N:42]4[CH2:46][C@H:45]([CH2:47][N:48]5[CH:52]=[CH:51][N:50]=[N:49]5)[O:44][C:43]4=[O:53])=[CH:28][C:27]=3[F:26])=[CH:21][N:20]=2)[CH2:15]1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 23626595(5R)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one2×HCID 69153408[(5S)-3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methyl beta-D-glucopyranoside2×

Product 1

HCID 86609336[(5S)-3-(5-{2-Fluoro-4-[(5R)-2-oxo-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]phenyl}pyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methyl beta-D-glucopyranosideYield 38.4%

Reagents, catalysts & solvents 2

HCID 178420553HCID 178420553, compoundCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

[(5S)-3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methyl β-D-glucopyranoside (Intermediate 20, 0.150 g, 0.36 mmol), (5R)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Intermediate 7, 0.153 g, 0.39 mmol), sodium carbonate (0.152 g, 1.43 mmol), and tetrakis(triphenylphosphino)palladium(0) (0.041 g, 0.036 mmol) were mixed in DMF/water (10:1, 5 mL) under nitrogen and heated at 70° C. bath temperature for 4 hours. The solvent was evaporated under reduced pressure. Chromatography on silica gel with dichloromethane/methanol 5:1 followed by crystallization from ethanol gave the product as colourless solid (83 mg). MS (ESP): 601.06 (MH+) for C27H29FN6O9

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customChromatography on silica gel with dichloromethane/methanol 5:1 followed by crystallization from ethanol

Sources & evidence

ORD record
ord-ef2b53543fa04e9995b17dd02852bfcd
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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