Thionyl Chloride → HCID 54348752, compound

HRID 1492508Notes

Reaction equation

HRID 1492508 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:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.S(Cl)(Cl)=O>>[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[NH:10][CH2:11][C:12]([N:16]([CH:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 10923588HCID 10923588, compoundHCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acid

Product 1

HCID 54348752HCID 54348752, compoundYield 17.6%

Procedure

The procedure is as in Example 1, but using 11.6 g of 2-[3-(3-methylphenyl)ureido]acetic acid, 15 g of ethyl (RS)-3-anilino-3-phenylpropionate and 4 cm3 of thionyl chloride as starting materials. The product obtained is purified by chromatography on 250 g of silica (0.04-0.063 mm) contained in a column 5 cm in diameter [eluent: methanol/dichloromethane (2/98 by volume)], using an excess pressure of 40 kPa of nitrogen and collecting 75-cm3 fractions. Fractions 19 to 21 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. and the residue obtained is recrystallized from ethyl acetate. 4.5 g of ethyl (RS)-3-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}-3-phenylpropionate melting at 146° C. are then obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on 250 g of silica (0.04-0.063 mm)
  3. customcollecting 75-cm3 fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C.
  5. customthe residue obtained
  6. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3ce4cd84314c4f899207abd3206d084c
Source dataset
uspto-grants-1994_12
Patent number
US05374656

Reaction notes

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