Thionyl Chloride → HCID 44209917, compound

HRID 1492507Notes

Reaction equation

HRID 1492507 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[NH:10][CH2:11][C:12]([OH:14])=O)[CH:5]=[CH:6][CH:7]=1.[NH:16]([CH:23]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=1)[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.S(Cl)(Cl)=O>>[F:37][C:33]1[CH:32]=[C:31]([CH:23]([N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12](=[O:14])[CH2:11][NH:10][C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)=[O:15])[C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 53747565tert-butyl (RS)-2-anilino-2-(3-fluorophenyl)acetate

Product 1

HCID 44209917HCID 44209917, compoundYield 26.4%

Procedure

The procedure is as in Example 1, but using 2.1 g of 2-[3-(3-methylphenyl)ureido]acetic acid, 3.02 g of tert-butyl (RS)-2-anilino-2-(3-fluorophenyl)acetate and 0.72 cm3 of thionyl chloride as starting materials. The product obtained is purified by chromatography on 100 g of silica (0.04-0.063 mm) contained in a column 3 cm in diameter [eluent: methanol/dichloromethane (1/99 by volume)], using an excess pressure of 40 kPa of nitrogen and collecting 10-cm3 fractions. Fractions 10 to 16 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. and the residue obtained is recrystallized from cyclohexane. 1.3 g of tert-buty (RS)-2-(3-fluorophenyl)-2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}acetate melting at 107° C. are then obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on 100 g of silica (0.04-0.063 mm)
  3. customcollecting 10-cm3 fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C.
  5. customthe residue obtained
  6. customis recrystallized from cyclohexane

Sources & evidence

ORD record
ord-341a9cbe25924fc7b287c2ebf1ce1390
Source dataset
uspto-grants-1994_12
Patent number
US05374656

Reaction notes

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