Dichloromethane → HCID 14178005, compound

HRID 2352134Notes

Reaction equation

[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][N:11]=2)=[CH:6][CH:5]=1.S(O[CH2:29][C@@H:30]1[O:35][C@H:31]1[CH2:32][CH2:33][CH3:34])(C)(=O)=O.C(Cl)Cl>CN(C)C=O.[K+].[Br-]>[CH2:16]([C:13]1[CH:14]=[N:15][C:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][CH2:29][C@H:30]3[C@H:31]([CH2:32][CH2:33][CH3:34])[O:35]3)=[CH:9][CH:8]=2)=[N:11][CH:12]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

0.16 g of NaH (5 mmol), as an 80% strength dispersion in oil, is added to a solution of 1.42 g (5 mmol) of 2-(4-hydroxyphenyl)-5-n-octylpyrimidine in 50 ml of dimethylformamide at a temperature of 0° C. When the evolution of gas has subsided, 1.35 g (7 mmol) of (2S, 3S)-1-mesyloxy-2,3-epoxyhexane are added, and the mixture is stirred for 6 hours at 0° C. The mixture is subsequently hydrolized in 100 ml of ice water and extracted with dichloromethane. After three-fold column chromatography (silica gel, dichloromethane), 0.61 g (32% of theory) of colorless crystals are obtained. The IR spectrum (in KBr) and the 1H NMR spectrum (in CDCl3) support the structural formula indicated, and the optical rotation is (α) D25 : -18.8° (c=10, CH2Cl2).

Workup

extractionextracted with dichloromethane
customAfter three-fold column chromatography (silica gel, dichloromethane), 0.61 g (32% of theory) of colorless crystals are obtained

Sources & evidence

ORD record: ord-d3a55e510266401ba06365c4673d6afc
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04876028

Reaction notes

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