Glycine methyl ester hydrochloride → HCID 86625868, compound

HRID 2421951Notes

Reaction equation

HRID 2421951 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[C:8](Cl)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24]>CC#N.CN(C=O)C>[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 122755Glycine methyl ester hydrochlorideHCID 672426272-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 86625868HCID 86625868, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

2-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (1.09 g, 3.64 mmol), methyl glycinate hydrochloride (0.68 g, 5.46 mmol) and TEA (10.10 g, 10.92 mmol) were dissolved in a mixture of MeCN (10 mL) and DMF (5 mL) and the reaction mixture was stirred at 65° C. over night. The reaction mixture was evaporated and the residue was diluted with saturated aqueous NaHCO3 and the mixture was extracted with DCM. The organic phases were combined, dried over MgSO4, filtered and evaporated to give the title compound.

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe residue was diluted with saturated aqueous NaHCO3
  3. extractionthe mixture was extracted with DCM
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e839402aa5c64acc94be517de3ed3b20
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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