Hydrochloric Acid → HCID 86735054, compound

HRID 262556Notes

Reaction equation

HRID 262556 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].Cl[CH2:10][CH2:11][CH2:12][C:13](Cl)=[O:14].[C:16]([OH:24])(=[S:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].Cl>[OH-].[Na+].O>[C:16]([S:23][CH2:10][CH2:11][CH2:12][C:13]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:14])(=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 783704-Chlorobutyryl chlorideHCID 145742L-ProlineHCID 178526132HCID 178526132, compound

Product 1

HCID 86735054HCID 86735054, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of L-proline (2.88 g.) in normal sodium hydroxide (25 ml.) chilled in an ice bath, 2 N sodium hydroxide (12.5 ml.) and 4-chlorobutyryl chloride (3.5 g.) are added. The reaction mixture is stirred at room temperature for 3.5 hours and a suspension of thiobenzoic acid (3.75 g.) and potassium carbonate (2.4 g.) in water (25 ml.) is added. After overnight stirring at room temperature, the reaction mixture is acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer is dried over magnesium sulfate and concentrated to dryness in vacuo. The residue is chromatographed on a column of silica gel with benzene-acetic acid (7:1). The fractions containing the desired material are pooled and concentrated to dryness, yield 1.35 g. A small aliquot of this material is dissolved in ethyl acetate and dicyclohexylamine is added until pH 8-10 (on a wet pH paper). The dicyclohexylamine salt crystallizes out, immediately, m.p. 159°-161°.

Workup

  1. additionis added
  2. stirringAfter overnight stirring at room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. concentrationconcentrated to dryness in vacuo
  6. customThe residue is chromatographed on a column of silica gel with benzene-acetic acid (7:1)
  7. additionThe fractions containing the desired material
  8. concentrationconcentrated to dryness, yield 1.35 g
  9. dissolutionA small aliquot of this material is dissolved in ethyl acetate
  10. additiondicyclohexylamine is added until pH 8-10 (on a wet pH paper)
  11. customThe dicyclohexylamine salt crystallizes out

Sources & evidence

ORD record
ord-cdd2dff6bf094261a08bdcc6436f213c
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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