Water → HCID 18612827, compound

HRID 1420595Notes

Reaction equation

HRID 1420595 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([CH:17]([CH2:22]O)[C:18]([O:20][CH3:21])=[O:19])[S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>N1C=CC=CC=1>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([S:6]([N:5]([CH2:4][C:3]2[CH:24]=[CH:25][CH:26]=[CH:27][C:2]=2[NH:1][S:29]([CH3:28])(=[O:31])=[O:30])[C:17](=[CH2:22])[C:18]([O:20][CH3:21])=[O:19])(=[O:8])=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 18612758Methyl [(2-aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionate

Product 1

HCID 18612827HCID 18612827, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.0 g (2.54 mmol) of methyl [(2-aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionate in 10 ml of pyridine cooled to -5° C. was added 0.432 ml (5.58 mmol) of methanesulfonyl chloride. The mixture was stirred at 0° C. for 48 hours. To the mixture was added ice and H2O and the mixture was extracted with ethyl acetate. The extract was washed with H2O, 2 N citric acid, brine and dried with Na2SO4. The solvent was removed under vacuum and the residue triturated with ethyl acetate-hexane to give 0.90 g of a solid, 128-142° C. Anal. for C19H22N2O7S2 : Calc'd: C,50.2; H,4.9; N,6.2; S,14.1; Found: C,49.6; H,5.0; N,6.9; S,14.0; Mass spectrum (ES) 455.5 (M+H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with H2O, 2 N citric acid, brine
  3. dry with materialdried with Na2SO4
  4. customThe solvent was removed under vacuum
  5. customthe residue triturated with ethyl acetate-hexane

Sources & evidence

ORD record
ord-962c8e5f34bf4935b2492385f21636dd
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

Loading…