HCID 59350552, compound → HCID 59749469, compound

HRID 747232Notes

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]([Sn:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si](OC[C@@H]1OC(=O)N(C2C=CC(I)=C([F:48])C=2)C1)(C(C)(C)C)(C)C>>[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]([Sn:22]([CH3:23])([CH3:24])[CH3:25])=[C:20]([F:48])[CH:21]=2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 59350552HCID 59350552, compound

HCID 59749517HCID 59749517, compound

Product 1

HCID 59749469HCID 59749469, compound

Procedure

Using essentially the same procedure as described for (5R)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-[4-(trimethylstannyl)phenyl]-1,3-oxazolidin-2-one, but starting from (5R)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-one (1.97 g, 4.37 mM) gave the title compound as a white solid after chromatography using hexanes then 20% ethyl acetate/hexanes (1.75 g).

Sources & evidence

ORD record: ord-9d3f4146bed34592b6e31164ced17387
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396847B2

Reaction notes

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