L-Hydroxyproline → HCID 70135784, compound

HRID 1637142Notes

Reaction equation

HRID 1637142 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([OH:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[OH:18][C@H:19]1[CH2:23][NH:22][C@H:21]([C:24](O)=[O:25])[CH2:20]1>>[ClH:3].[CH2:5]([O:17][C:24](=[O:25])[C@@H:21]1[CH2:20][C@@H:19]([OH:18])[CH2:23][NH:22]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 5810L-HydroxyprolineHCID 81931-DodecanolHCID 24386Thionyl Chloride

Product 1

HCID 70135784HCID 70135784, compound

Conditions

Temperature
100 °C

Procedure

Thionyl chloride (15.5 g, 130 mmol) at 25 to 30° C. was added with stirring to 1-dodecanol (190 g, 1.02 mol). After adding trans-4-hydroxy-L-proline (15 g, 114.4 mol), the suspension was stirred for 5 hours at 100° C. The 1-dodecanol was distilled off under reduced pressure from the now clear reaction solution, and the cooled crystalline residue was dissolved in methanol and filtered. The solvent was distilled off under reduced pressure and distillation was interrupted when crystallization started. The residue was precipitated from diethyl ether, then the precipitate was filtered off and washed with diethyl ether. Yield: 35.3 g (105.1 mmol, 92% of theory) of a white crystalline powder. 1H-NMR (CD3SOCD3)δ=0.86 (3H, t), 1.25 (18H, m), 1.61 (2H, m), 2.08 (1H, m), 2.18 (1H, m), 3.06 to 3.3 (partly under H2O signal, m), 4.16 (2H, m) 4.45 (2H, m), 5.53 (1H, m), 9.5 to 10 ppm (2H, broad); 13C-NMR (CD3SOCD3)δ=168.8 (s), 68.4 (d), 65.8 (t), 57.4 (d), 53.2 (d), 37.0(t), 31.2 (t), 28.94 (t), 28.90 (t), 28.86 (t), 28.81 (t), 28.60 (t), 28.51 (t), 27.8 (t), 25.08(t) 22.0 (t), 13.9 ppm (q). MS (ESI) m/e=300.1 (M+of the cation).

Workup

  1. distillationThe 1-dodecanol was distilled off under reduced pressure from the now clear reaction solution
  2. dissolutionthe cooled crystalline residue was dissolved in methanol
  3. filtrationfiltered
  4. distillationThe solvent was distilled off under reduced pressure and distillation
  5. customwhen crystallization
  6. customThe residue was precipitated from diethyl ether
  7. filtrationthe precipitate was filtered off
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-c93920a1aeb0472fb94b808789b879c8
Source dataset
uspto-grants-2000_03
Patent number
US06039939

Reaction notes

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