Acetone → (5R)-3-[3-Fluoro-4-(4-methyl-1,2,3-triazol-1-yl)phenyl]-5-(hydroxymethyl)oxazolidin-2-one

HRID 1452573Notes

Reaction equation

C([O:8][C:9](=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([CH3:22])[N:19]=[N:18]2)=[C:13]([F:23])[CH:12]=1)C1C=CC=CC=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:35][C:36]([CH3:38])=[O:37].C(OCC)(=[O:41])C>>[F:23][C:13]1[CH:12]=[C:11]([N:10]2[CH2:35][C@H:36]([CH2:38][OH:41])[O:37][C:9]2=[O:8])[CH:16]=[CH:15][C:14]=1[N:17]1[CH:21]=[C:20]([CH3:22])[N:19]=[N:18]1

Participants

Reactant 4

HCID 180Acetone

HCID 8857Ethyl Acetate

HCID 2733832Lithium Hexamethyldisilazide

HCID 57526959[3-Fluoro-4-(4-methyl-[1,2,3]triazol-1-yl)-phenyl]-carbamic acid benzyl ester2×

Product 1

HCID 57526994(5R)-3-[3-Fluoro-4-(4-methyl-1,2,3-triazol-1-yl)phenyl]-5-(hydroxymethyl)oxazolidin-2-one

Procedure

[3-Fluoro-4-(4-methyl-[1,2,3]-triazol-1-yl)-phenyl]-carbamic acid benzyl ester (Intermediate 20) (56 g, 0.17 mol), lithium hexamethyldisilazide (LiHMDS) (1M/THF, 200 ml, 0.20 mol) and R-(−)-glycidyl butyrate (25 ml, 0.18 mol) were reacted following the procedure described for Intermediate 25. Chromatography on silica gel with 0-40% acetone in ethyl acetate, followed by trituration with acetone/ethyl acetate/chloroform/hexanes (300 ml/100 ml/100 ml/500 ml) overnight gave the title compound as an off-white solid (33.9 g), m.p. 190.2-192.0° C.

Sources & evidence

ORD record: ord-da97058d24a94fd2bb46d8032b7ad7ea
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473699B2

Reaction notes

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