Water → 2-{3-[((S)-1-Dimethylaminomethyl-2-phenyl-ethylamino)-methyl]-benzyl}-1,1-dioxo-1lambda6-isothiazolidine-3-carboxylic acid

HRID 1879468Notes

Reaction equation

HRID 1879468 reaction equation
C([O:3][C:4]([CH:6]1[CH2:10][CH2:9][S:8](=[O:12])(=[O:11])[N:7]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C@H:22]([CH2:30][N:31]([CH3:33])[CH3:32])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:15]=1)=[O:5])C.O.[OH-].[Li+].O>O1CCCC1.Cl>[CH3:32][N:31]([CH2:30][C@@H:22]([NH:21][CH2:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][N:7]1[CH:6]([C:4]([OH:5])=[O:3])[CH2:10][CH2:9][S:8]1(=[O:12])=[O:11])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH3:33]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 582804542-{3-[((S)-1-dimethylaminomethyl-2-phenyl-ethylamino)-methyl]-benzyl}-1,1-dioxo-1lambda6-isothiazolidine-3-carboxylic acid ethyl ester

Product 1

HCID 582804442-{3-[((S)-1-Dimethylaminomethyl-2-phenyl-ethylamino)-methyl]-benzyl}-1,1-dioxo-1lambda6-isothiazolidine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude 2-{3-[((S)-1-dimethylaminomethyl-2-phenyl-ethylamino)-methyl]-benzyl}-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid ethyl ester (360 mg, approx. 0.67 mmol) in tetrahydrofuran (4 mL) was added lithium hydroxide hydrate (57.4 mg, 1.37 mmol) followed by water (1 mL). It was stirred at room temperature for 2 h. To the stirred solution was added ˜15 drops 1N hydrochloric acid to bring the pH to 4.5. The sample was concentrated to dryness and dried over phosphorus pentoxide overnight. The crude 2-{3-[((S)-1-dimethylaminomethyl-2-phenyl-ethylamino)-methyl]-benzyl}-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid (350 mg, ca 80% pure) (LiCl present) was used in the next step.

Workup

  1. concentrationThe sample was concentrated to dryness
  2. dry with materialdried over phosphorus pentoxide overnight

Sources & evidence

ORD record
ord-fc4a5b426034435e9b30cffc57e2197e
Source dataset
uspto-grants-2012_11
Patent number
US08314250B2

Reaction notes

Loading…