Hydrochloric Acid → HCID 86746584, compound

HRID 1612623Notes

Reaction equation

HRID 1612623 reaction equation
[C:1]([NH:4][C:5]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Cl)=[CH:17][CH:16]=1)(C([O-])=O)[C:6]([O:8]CC)=[O:7])(=[O:3])[CH3:2].[S:23]([O-:26])([O-:25])=[O:24].[Na+:27].[Na+].[OH-].[Na+].Cl>O.C(O)C>[C:1]([NH:4][C@H:5]([C:6]([OH:8])=[O:7])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][S:23]([O-:26])(=[O:25])=[O:24])=[CH:17][CH:16]=1)(=[O:3])[CH3:2].[Na+:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 19776341HCID 19776341, compound

Product 1

HCID 86746584HCID 86746584, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

1.1 g of ethyl 2-acetamido-2-(4-chloromethylbenzyl)malonate are added to a solution of 3.31 g of sodium sulfite in 20 cm3 of distilled water, and 8 cm3 of a 10% aqueous solution of caustic soda, and the reaction mixture is heated for 3 hours to a temperature of about 120° C. After cooling to a temperature of about 20° C., the reaction mixture is taken to pH=1 by means of a 1N aqueous solution of hydrochloric acid, and the mixture is again heated to 120° C. for 1 hour. The reaction mixture is cooled to a temperature of about 20° C., and taken up in 150 cm3 of ethanol; the inorganic salts are separated off by filtration and the filtrate is concentrated to dryness under reduced pressure (20 mm of mercury; 2.7 kPa) at 30° C. The residue obtained is passed through a 2.5 cm diameter chromatography column packed with 100 g of silica gel, eluting with a mixture of dichloromethane, methanol, water and acetic acid (respectively 70-30-6-3 by volume). 424 mg of monosodium N-acetyl-4-sulfonatomethylphenylalanine are thus obtained.

Workup

  1. temperatureAfter cooling to a temperature of about 20° C.
  2. temperaturethe mixture is again heated to 120° C. for 1 hour
  3. temperatureThe reaction mixture is cooled to a temperature of about 20° C.
  4. customthe inorganic salts are separated off by filtration
  5. concentrationthe filtrate is concentrated to dryness under reduced pressure (20 mm of mercury; 2.7 kPa) at 30° C
  6. customThe residue obtained
  7. washeluting with a mixture of dichloromethane, methanol, water and acetic acid (respectively 70-30-6-3 by volume)

Sources & evidence

ORD record
ord-5c6b61edbab744649a9641645a9190a5
Source dataset
uspto-grants-1993_03
Patent number
US05190921

Reaction notes

Loading…