Diisopropylethylamine → (5R)-3-(4-Iodophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

HRID 747208Notes

Reaction equation

[NH2:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([I:15])=[CH:11][CH:10]=2)[CH2:4]1.C(N(C(C)C)CC)(C)C.Cl[CH:26](Cl)[C:27](=[N:29][NH:30]S(C1C(C)=CC=CC=1)(=O)=O)[CH3:28]>CO>[I:15][C:12]1[CH:13]=[CH:14][C:9]([N:5]2[CH2:4][C@H:3]([CH2:2][N:1]3[CH:26]=[C:27]([CH3:28])[N:29]=[N:30]3)[O:7][C:6]2=[O:8])=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(5S)-5-(Aminomethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one (6.0 g, 18.9 mmol) was dissolved in methanol (150 ml, c=0.1M) and cooled to 0° C. Diisopropylethylamine (13.1 ml, 75.4 mmol) was added and the reaction stirred at 0° C. for 5 min; toluenesulfonic acid 2-(2,2-dichloro-1-methylethylidene)hydrazide was then added and the reaction stirred overnight. The volatiles were concentrated in vacuo, dichloromethane was added and some product crystallized from solution; the remaining residue was purified by flash chromatography on silica gel using 0-5% methanol in dichloromethane as the eluent. The relevant fractions were combined giving 5.5 g of the desired product.

Workup

stirringthe reaction stirred overnight
concentrationThe volatiles were concentrated in vacuo, dichloromethane
additionwas added
customsome product crystallized from solution
customthe remaining residue was purified by flash chromatography on silica gel using 0-5% methanol in dichloromethane as the eluent

Sources & evidence

ORD record: ord-01cbd0cf2b684730b04f0a663c807c72
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396847B2

Reaction notes

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