Hydrochloric Acid → HCID 53700414, compound

HRID 987055Notes

Reaction equation

[CH3:1][CH2:2][C@@H:3]([C:5]([O:7][C@@H:8]1[C@@H:13]2[C@@H:14]([CH2:19][CH2:20][C@H:21]3[O:27][C:25](=[O:26])[CH2:24][C@H:23]([OH:28])[CH2:22]3)[C@@H:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[CH:11][C@H:10]([CH3:29])[CH2:9]1)=[O:6])[CH3:4].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.Cl>>[CH2:30]([CH:24]1[C:25](=[O:26])[O:27][CH:21]([CH2:20][CH2:19][CH:14]2[CH:13]3[C:12](=[CH:11][CH:10]([CH3:29])[CH2:9][CH:8]3[O:7][C:5](=[O:6])[CH:3]([CH3:4])[CH2:2][CH3:1])[CH:17]=[CH:16][CH:15]2[CH3:18])[CH2:22][CH:23]1[OH:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 7498Benzyl Bromide

HCID 53232Lovastatin

Product 1

HCID 53700414HCID 53700414, compound

Procedure

After 15 minutes, 202 mg (0.50 mmol) of mevinolin are added and the reaction mixture is kept at −77° C. for 30 minutes. Then 171 mg (1.0 mmol) benzyl bromide are added. After 2 hours the reaction is let come to room temperature and poured onto 0.1 N aqueous HCl. The phases are separated and the aqueous phase is extracted twice with ethyl acetate. The organic phases are combined, washed with brine and dried over sodium sulfate. The solvent is evaporated and the crude product is purified by silica gel chromatography (diethyl ether/hexane 2/1) to afford the desired product as a colorless oil.

Workup

waitthe reaction mixture is kept at −77° C. for 30 minutes
waitAfter 2 hours the reaction is let come to room temperature
customThe phases are separated
extractionthe aqueous phase is extracted twice with ethyl acetate
washwashed with brine
dry with materialdried over sodium sulfate
customThe solvent is evaporated
customthe crude product is purified by silica gel chromatography (diethyl ether/hexane 2/1)

Sources & evidence

ORD record: ord-419833650dfb4b13b10d94801749f319
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06630492B1

Reaction notes

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