Isopropanol → HCID 14178475, compound

HRID 1190799Notes

Reaction equation

HRID 1190799 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].O=S(Cl)Cl.[CH:14](O)([CH3:16])[CH3:15]>>[CH:14]([O:8][C:7](=[O:9])[C@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[NH2:1])([CH3:16])[CH3:15]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 6106L-LeucineHCID 24386Thionyl Chloride

Product 1

HCID 14178475HCID 14178475, compoundYield 71%

Conditions

Temperature
100 °C

Procedure

A mixture of L-Leucine (1 g, 1 eq.), SOCl2 (1.7 ml, 3 eq.) in isopropanol (15 ml) was stirred under microwave irradiation at 100° C. for 1 hour. Solvent was then evaporated, the residue filtered and Et2O was added to give L-Leucine isopropyl ester as a yellow oil in 71% yield. 1H NMR (DMSO-d6, 400 MHz) δ (ppm): 0.88 (dd, J=6.41 Hz and J=2.14 Hz, 6H), 1.22 (t, J=6.03 Hz, 6H), 1.60-1.75 (m, 3 H), 3.82 (t, J=7.10 Hz, 1H), 4.97 (m, 1H), 8.61 (s, 2H).

Workup

  1. customSolvent was then evaporated
  2. filtrationthe residue filtered
  3. additionEt2O was added

Sources & evidence

ORD record
ord-ecf9496331c3436fb64adfa8c1b72875
Source dataset
uspto-grants-2014_03
Patent number
US08680071B2

Reaction notes

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