Water → HCID 743488, compound

HRID 1420603Notes

Reaction equation

HRID 1420603 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.O>C(Cl)Cl>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([S:23]([NH:2][CH2:3][C:4]([O:6][CH3:7])=[O:5])(=[O:25])=[O:24])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 743488HCID 743488, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 12.5 g (0.1 mol) of glycine, methyl ester hydrochloride in 120 ml of CH2Cl2, cooled in an ice bath was added 41.7 ml (0.3 mol) of triethylamine, followed by the dropwise addition of a solution of 20.65 g (0.1 mol) of 4-methoxybenzenesulfonyl chloride in 40 ml of CH2Cl2. The mixture was stirred at room temperature overnight and poured into water. The organic layer was separated and washed with 2 N citric acid, H2O, 1 N NaHCO3, brine and dried with Na2SO4. The solvent was removed under vacuum to give 24.6 g of residue which was triturated with ethyl acetate to give 19.9 g of crystals, m.p. 59°-61° C. Anal. for C10H13NSO5 : Calc'd: C,46.3; H,5.1; N,5.4; Found: C,46.2; H,5.0; N,5.2.

Workup

  1. temperaturecooled in an ice bath
  2. customThe organic layer was separated
  3. washwashed with 2 N citric acid, H2O, 1 N NaHCO3, brine
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-e6eaf1a8ed4949e19d42631ccfe35880
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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