Compound 3 → HCID 59350552, compound

HRID 747233Notes

Reaction equation

[Si:1]([O:8][CH2:9][C@@H:10]1[O:14][C:13](=[O:15])[N:12]([C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][CH:17]=2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F:23]C1C=C(N2C[C@H](CO)OC2=O)C=CC=1I>>[Si:1]([O:8][CH2:9][C@@H:10]1[O:14][C:13](=[O:15])[N:12]([C:16]2[CH:17]=[CH:18][C:19]([I:22])=[C:20]([F:23])[CH:21]=2)[CH2:11]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 20788885Compound 3

HCID 59749514HCID 59749514, compound

Product 1

HCID 59350552HCID 59350552, compound

Procedure

Using essentially the same procedure as that used for (5R)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one (above), but starting from (5R)-3-(3-fluoro-4-iodophenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one (2.0 g, 1.0 mM) gave the title compound as a light yellow soild after chromatography using 50% ethyl acetate/hexanes (1.94 g).

Sources & evidence

ORD record: ord-83c080c40cab450e99a0614736ab004d
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396847B2

Reaction notes

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