Triethylamine → HCID 54327434, compound

HRID 1081250Notes

Reaction equation

HRID 1081250 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:8])[CH:5]([CH3:7])[NH2:6].CCN(CC)CC.[C:16](Cl)(=[O:24])[CH:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20]>O.C(Cl)Cl>[CH3:2][O:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH:6][C:16](=[O:24])[CH:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 762402-Propylvaleryl chlorideHCID 2756298Alanine, methyl ester, hydrochloride (1:1)

Product 1

HCID 54327434HCID 54327434, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of DL-alanine methyl ester hydrochloride (13.7 g, 98 mmole) and Et3N (20.2 g, 200 mmole) in water (50 ml) was added dropwise to an ice-cooled solution of valproyl chloride (15.0 g, 92 mmole) in CH2Cl2 (150 ml). After completion of addition the reaction mixture was stirred for 4 hrs. at RT. The layers were then separated and the aqueous layer extracted with CH2Cl2. The combined organic phases were washed successively with water, satd. NaHCO3, 0.1N HCl and satd. NaCl, dried and evaporated to dryness. The residue was treated with hexane (60 ml), and the resultant solid was collected by filtration, washed with hexane and dried to give 14.2 g (62 mmole, 63%) of the title compound as a white solid, mp 72°-3° C.

Workup

  1. additionAfter completion of addition the reaction mixture
  2. customat RT
  3. customThe layers were then separated
  4. extractionthe aqueous layer extracted with CH2Cl2
  5. washThe combined organic phases were washed successively with water
  6. dry with materialNaCl, dried
  7. customevaporated to dryness
  8. additionThe residue was treated with hexane (60 ml)
  9. filtrationthe resultant solid was collected by filtration
  10. washwashed with hexane
  11. customdried

Sources & evidence

ORD record
ord-4e7f39d9fabb4b3aab5f41389c7fbd48
Source dataset
uspto-grants-1996_12
Patent number
US05585358

Reaction notes

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