Trifluoroacetic acid → 2-[(2-Aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionic acid

HRID 1420584Notes

Reaction equation

HRID 1420584 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][N:5]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:6]([CH2:14][OH:15])[C:7]([O:9]C(C)(C)C)=[O:8].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][N:5]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:6]([CH2:14][OH:15])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867554362-[(2-Aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionic acid, tert-butyl ester

Product 1

HCID 186128792-[(2-Aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionic acidYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.75 g (1.72 mmol) of 2-[(2-aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionic acid, tert-butyl ester and 6 ml of trifluoroacetic acid in 6 ml of CH2Cl2 was stirred at room temperature for 3 hours and then concentrated to dryness under vacuum. To the residue was added H2O, CH2Cl2 and 1N NaOH until the aqueous layer reached pH 8. The aqueous layer was then separated, acidified with 2 N citric acid and extracted with ethyl acetate. The extract was washed with H2O, brine and dried Na2SO4. The solvent was removed under vacuum to give 0.35 g (54%) of a solid. Anal. for C17H20N2O6S: Calc'd: C, 53.7; H,5.3; N,7.4; Found: C, 53.0; H,5.3; N,6.9.

Workup

  1. concentrationconcentrated to dryness under vacuum
  2. additionTo the residue was added H2O, CH2Cl2 and 1N NaOH until the aqueous layer
  3. customThe aqueous layer was then separated
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with H2O, brine and dried Na2SO4
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-a687ba07014740688fe2142c241d625a
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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