Hydrochloric Acid → HCID 59837328, compound

HRID 2356230Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][C:25]([C:32]([O:34]CC)=[O:33])([CH3:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:18]([Cl:37])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl.C(OCC)(=O)C>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])([CH3:31])[C:32]([OH:34])=[O:33])=[C:18]([Cl:37])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The compound of Example 194 (2.74 g) was dissolved in ethanol (10 mL). To this solution, potassium hydroxide (330 mg) was added and the mixture was stirred overnight at 50° C. Subsequently, the reaction mixture was diluted with water, followed by addition of 2 mol/L hydrochloric acid and extraction with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride, was dried over anhydrous magnesium sulfate, and was then concentrated. The resulting residue was purified on a silica gel chromatography (hexane:ethyl acetate=10:1 to 2:1) to give the desired product as a yellow oil (2.38 g).

Workup

washThe ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride
dry with materialwas dried over anhydrous magnesium sulfate
concentrationwas then concentrated
customThe resulting residue was purified on a silica gel chromatography (hexane:ethyl acetate=10:1 to 2:1)

Sources & evidence

ORD record: ord-2a27bea79280416597c91cf6591d0c8c
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759326B2

Reaction notes

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