Triethylamine → HCID 11790997, compound

HRID 1741797Notes

Reaction equation

HRID 1741797 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6].C(N(CC)CC)C.[O:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[C:23](Cl)=[O:24]>O1CCCC1>[CH3:2][O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH:6][C:23]([CH:19]1[CH2:20][CH2:21][CH2:22][O:18]1)=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111190Methyl valinate hydrochlorideHCID 551254Tetrahydro-2-furancarbonyl chloride

Product 1

HCID 11790997HCID 11790997, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

617 g (3.68 mol) of (S)-valine methyl ester hydrochloride were suspended in about 2.2 l of tetrahydrofuran and 745 g (7.38 mol) of triethylamine were added. 451 g (3.35 mol) of tetrahydrofuran-2-carbonyl chloride in 200 ml of THF were added dropwise with stirring, the reaction temperature rising to about 65° C. After completion of the addition, the mixture was stirred at room temperature for a further 12 hours. The precipitate was filtered off with suction and thoroughly washed with tetrahydrofuran, and the combined organic phases were evaporated. The residue was dissolved in ether to remove excess (S)-valine methyl ester, shaken with water and dried in the customary manner. Vacuum distillation yields N-(2-tetrahydrofuroyl)-(S)-valine methyl ester (formula V with X=S, n=1, R=CH(CH3)2 and R'=CH3) as a colorless liquid, b.p. 98°-103° C./0.01 torr, yield: 611 g (80%).

Workup

  1. customrising to about 65° C
  2. additionAfter completion of the addition
  3. stirringthe mixture was stirred at room temperature for a further 12 hours
  4. filtrationThe precipitate was filtered off with suction
  5. washthoroughly washed with tetrahydrofuran
  6. customthe combined organic phases were evaporated
  7. dissolutionThe residue was dissolved in ether
  8. customto remove excess (S)-valine methyl ester
  9. stirringshaken with water
  10. customdried in the customary manner
  11. distillationVacuum distillation

Sources & evidence

ORD record
ord-5f6e9b40c05e4276984659c51d5e078a
Source dataset
uspto-grants-1994_08
Patent number
US05334730

Reaction notes

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