Thionyl Chloride → HCID 22479134, compound

HRID 1392167Notes

Reaction equation

HRID 1392167 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:19][CH2:18][CH2:17][C@@:13]2([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][CH:22]=2)[C:14]([OH:16])=O)=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.O=S(Cl)Cl>>[C:27]([C:24]1[CH:25]=[CH:26][C:21]([CH2:20][C:13]23[CH2:17][CH2:18][CH2:19][N:12]2[C:10](=[O:11])[N:9]([C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:14]3=[O:16])=[CH:22][CH:23]=1)([OH:29])=[O:28]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 69213875HCID 69213875, compound

Product 1

HCID 22479134HCID 22479134, compoundYield 62.6%

Conditions

Temperature
100 °C

Procedure

A mixture of N-[N-(3,5-dichlorophenyl)carbamoyl]-2-(4-carboxybenzyl)proline (0.080 g) and SOCl2 (2.0 mL) was heated at 100° C. for 1 hour. The solution was evaporated. The residue was dissolved in toluene, evaporated and dried under vacuum. The residue was dissolved in a mixture of THF/H2O (4/0.4 mL) and the solution was stirred for 18 hours. It was diluted with EtOAc and water. The organic layer was separated, washed with water, brine, dried (MgSO4), filtered, and concentrated. Purification by chromatography (Silica gel: EtOAc/hexane: 1/1) afforded the titled compound (48 mg). MS (m/z) 441 (M++Na).

Workup

  1. customThe solution was evaporated
  2. dissolutionThe residue was dissolved in toluene
  3. customevaporated
  4. customdried under vacuum
  5. dissolutionThe residue was dissolved in a mixture of THF/H2O (4/0.4 mL)
  6. additionIt was diluted with EtOAc and water
  7. customThe organic layer was separated
  8. washwashed with water, brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurification by chromatography (Silica gel: EtOAc/hexane: 1/1)

Sources & evidence

ORD record
ord-950eef68c33449c295b0c24bae17c9c9
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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