Hydrochloric Acid → 2-(2-Methanesulfonylamino-benzothiazole-6-yl)-propionic acid ethyl ester

HRID 1626899Notes

Reaction equation

HRID 1626899 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:7]1[CH:16]=[CH:15][C:10]2[N:11]=[C:12]([NH2:14])[S:13][C:9]=2[CH:8]=1)[CH3:6])[CH3:2].[CH3:18][S:19](Cl)(=[O:21])=[O:20].Cl>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:7]1[CH:16]=[CH:15][C:10]2[N:11]=[C:12]([NH:14][S:19]([CH3:18])(=[O:21])=[O:20])[S:13][C:9]=2[CH:8]=1)[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 13477940Ethyl 2-amino-alpha-methylbenzothiazole-6-acetate

Product 1

HCID 577421492-(2-Methanesulfonylamino-benzothiazole-6-yl)-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4 (347 mg, 1 mmol) in pyridine (3 ml) is added to MsCl (0.13 ml, 1.21 mmol) at room temperature. The reaction mixture is stirred for 14 h at room temperature. 1N HCl (30 ml) is added to the mixture. The mixture extracted with ethyl acetate. The organic layer is dried over magnesium sulfate. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography(n-Hexane:EtOAc).

Workup

  1. extractionThe mixture extracted with ethyl acetate
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash column chromatography(n-Hexane:EtOAc)

Sources & evidence

ORD record
ord-ef62157892d945c884d7d37318dba27b
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

Loading…