Hydrochloric Acid → HCID 58024211, compound

HRID 14990Notes

Reaction equation

HRID 14990 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[C:17]2[CH:16]=[C:15]([CH:18]([CH2:33][CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[C:19]([NH:21][C:22]3[S:23][CH:24]=[C:25]([CH2:27][C:28]([O:30]CC)=[O:29])[N:26]=3)=[O:20])[CH:14]=[CH:13][C:12]=2[S:11](=[O:41])(=[O:40])[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2.Cl>O1CCCC1.O>[CH3:3][N:4]1[C:17]2[CH:16]=[C:15]([CH:18]([CH2:33][CH:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)[C:19]([NH:21][C:22]3[S:23][CH:24]=[C:25]([CH2:27][C:28]([OH:30])=[O:29])[N:26]=3)=[O:20])[CH:14]=[CH:13][C:12]=2[S:11](=[O:40])(=[O:41])[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58024262HCID 58024262, compound

Product 1

HCID 58024211HCID 58024211, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

At room temperature and with stirring, 0.25 ml of 2M NaOH are added to a suspension of 25.0 mg of ethyl {2-[2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionylamino]thiazol-4-yl}acetate in 5 ml of tetrahydrofuran and 2 ml of water, and the mixture is stirred at room temperature for 12 hours. The reaction mixture is then neutralized by addition of 1M HCl. The solvents are removed under reduced pressure, and the residue is taken up in 20 ml of ethyl acetate and washed three times with in each case 10 ml of water. The organic phase is dried with MgSO4 and concentrated under reduced pressure. The residue is purified by RP-HPLC. This gives 22.5 mg of {2-[2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionylamino]thiazol-4-yl}acetic acid as a lyophilisate.

Workup

  1. stirringthe mixture is stirred at room temperature for 12 hours
  2. customThe solvents are removed under reduced pressure
  3. washwashed three times with in each case 10 ml of water
  4. dry with materialThe organic phase is dried with MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-d1e524c7992d49d7b41ae57ffc510d67
Source dataset
uspto-grants-2010_06
Patent number
US07732440B2

Reaction notes

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