Sodium Hydroxide → 2-(10-Methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionic acid

HRID 14988Notes

Reaction equation

[CH3:1][N:2]1[C:15]2[CH:14]=[C:13]([CH:16]([CH2:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:17]([O:19]CC)=[O:18])[CH:12]=[CH:11][C:10]=2[S:9](=[O:30])(=[O:29])[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[OH-].[Na+]>CO>[CH3:1][N:2]1[C:15]2[CH:14]=[C:13]([CH:16]([CH2:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:17]([OH:19])=[O:18])[CH:12]=[CH:11][C:10]=2[S:9](=[O:30])(=[O:29])[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

Conditions

Temperature: 80 °C

Procedure

2.0 g of ethyl 2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionate are suspended in 100 ml of methanol, and 32.1 ml of a 2M NaOH solution are added. The reaction mixture is stirred at 80° C. for one hour. The methanol is removed under reduced pressure and the reaction mixture is adjusted to pH 4 by addition of concentrated hydrochloric acid. The mixture is extracted three times with in each case 100 ml of ethyl acetate. The combined organic phases are dried over MgSO4 and then concentrated under reduced pressure. This gives 1.85 g of 2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionic acid as a solid.

Workup

customThe methanol is removed under reduced pressure
additionthe reaction mixture is adjusted to pH 4 by addition of concentrated hydrochloric acid
extractionThe mixture is extracted three times with in each case 100 ml of ethyl acetate
dry with materialThe combined organic phases are dried over MgSO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0773a887e5a640d0900c1ea36d2e3653
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732440B2

Reaction notes

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