m-Tolyl isocyanate → HCID 15132282, compound

HRID 1742364Notes

Reaction equation

HRID 1742364 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[NH2:11][CH:12]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:13]([OH:15])=[O:14].C(=O)(O)[O-].[Na+]>O>[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:10])[NH:11][CH:12]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:13]([OH:15])=[O:14])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 69303m-Tolyl isocyanateHCID 1026994-methyl hydrogen L-aspartate hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 15132282HCID 15132282, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(RS)-2-[3-(3-Methylphenyl)uriedo]-3-methoxycarbonylpropionic acid may be prepared in the following manner: 3-methylphenyl isocyanate (13.3 g) is added in the course of 30 minutes at 17° C. to a solution of (RS)-2-amino-3-methoxycarbonylpropionic acid (16.1 g) and sodium bicarbonate (8.4 g) in water (160 cc). The reaction medium is stirred for a further 16 hours and the insoluble matter is then filtered off. The liltrate is taken to pH 1 with 4N hydrochloric acid and extracted with ethyl acetate (3×15 cc). The extracts are combined, washed with water (2×15 cc), dried over magnesium sulphate and then taken to dryness under reduced pressure (2.7 kPa) at 70° C. After crystallisation in petroleum ether, (RS)-2-[3-(3-methylphenyl)ureido]-3-methoxycarbonylpropionic acid (24 g) is obtained.

Workup

  1. filtrationthe insoluble matter is then filtered off
  2. extractionextracted with ethyl acetate (3×15 cc)
  3. washwashed with water (2×15 cc)
  4. dry with materialdried over magnesium sulphate
  5. customtaken to dryness under reduced pressure (2.7 kPa) at 70° C
  6. customAfter crystallisation in petroleum ether

Sources & evidence

ORD record
ord-2ef1282ef9694aab94136b4a6b651425
Source dataset
uspto-grants-1994_08
Patent number
US05338760

Reaction notes

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