HCID 69831201, compound → HCID 69830277, compound

HRID 2084361Notes

Reaction equation

[CH2:1]([O:8][CH2:9][C@H:10]([OH:36])[CH2:11][C:12]1[N:13](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:14]=[CH:15][N:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(C)=O.Cl>[CH2:1]([O:8][CH2:9][C@H:10]([OH:36])[CH2:11][C:12]1[NH:13][CH:14]=[CH:15][N:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (2R)-1-(benzyloxy)-3-(1-trityl-1H-imidazol-2-yl)-2-propanol (1.40 g) in acetone (8 ml), 1 N hydrochloric acid (8 ml) was added, followed by stirring at 50° C. for 1 hour. Additionally, 1 N hydrochloric acid (8 ml) was added, followed by stirring at 50° C. for 2 hours. After concentration and addition of water, the reaction mixture was twice washed with diethyl ether. After neutralization with aqueous sodium bicarbonate, the water layer was extracted with ethyl acetate and washed with saline, after which it was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:ethyl acetate-methanol=10:1) to yield the titled compound (424 mg) as a colorless oily substance.

Workup

stirringby stirring at 50° C. for 2 hours
concentrationAfter concentration and addition of water
washthe reaction mixture was twice washed with diethyl ether
extractionAfter neutralization with aqueous sodium bicarbonate, the water layer was extracted with ethyl acetate
washwashed with saline
dry with materialafter which it was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent:ethyl acetate-methanol=10:1)

Sources & evidence

ORD record: ord-e7536dd0133c46d9a499a7c577b6dd73
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716863B2

Reaction notes

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