Palmitoyl chloride → HCID 15870713, compound

HRID 1637143Notes

Reaction equation

HRID 1637143 reaction equation
Cl.[CH2:2]([O:14][C:15](=[O:22])[C@@H:16]1[CH2:20][C@@H:19]([OH:21])[CH2:18][NH:17]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(=O)([O-])O.[Na+].[C:28](Cl)(=[O:44])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>O1CCOCC1.O>[CH2:2]([O:14][C:15](=[O:22])[C@@H:16]1[CH2:20][C@@H:19]([OH:21])[CH2:18][N:17]1[C:28](=[O:44])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 8206Palmitoyl chlorideHCID 516892Sodium BicarbonateHCID 70135784HCID 70135784, compound

Product 1

HCID 15870713HCID 15870713, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

trans-4-Hydroxy-L-proline dodecyl ester hydrochloride (10 g, 29.8 mmol) was dissolved in 1,4-dioxane (125 ml) and water (125 ml); with stirring, sodium hydrogencarbonate (10.4 g, 123.8 mmol) was firstly added, followed by 1-hexadecanoyl chloride (9 ml, 8.19 g, 29.8 mmol). The reaction mixture was stirred for 1 hour at room temperature. The suspension was adjusted to pH 1 to 1.5 and then filtered. The residue was washed with water until neutral and dried under reduced pressure in the melt. Yield: 15.1 g (28 mmol, 94% of theory, 97 to 100% purity [HFLC]) of a white waxy crystalline mass, m.p.: 39 to 44° C. 1H-NMR (CDCl3)δ=0.89 (6H, t), 1.2 to 1.4 (40H, m), 1.5 to 1.7 (61-1, m), 2.05 to 2.40 (4H, dm), 3.79 (1H, dd), 4.12 (2H, m), 4.5 to 4.6 ppm (2H, m); 13C-NMR (CDCl3)δ=172.50 (s), 172.48 (s), 70.4 (d), 65.4 (t), 57.6 (d), 55.1 (t), 37.9 (t), 34.6 (t), 32.0, 29.72 (2C), 29.70 (2C), 29.68 (4C), 29.66, 29.62, 29.56 (2C), 29.48, 29.40, 29.38 (2C,), 29.28, 28.56, 25.85, 24.68, 22.70 (2C), 14.1 (2C, q,q). Elemental analysis: calc.: C 73.7%, H 11.8%, N 2.6%, O 11.9%; found: C 73.5%, H 11.8%, N 2.5%, O 12.2%.

Workup

  1. stirringThe reaction mixture was stirred for 1 hour at room temperature
  2. filtrationfiltered
  3. washThe residue was washed with water until neutral and
  4. customdried under reduced pressure in the melt

Sources & evidence

ORD record
ord-1f87bcc015294847980011578a379a21
Source dataset
uspto-grants-2000_03
Patent number
US06039939

Reaction notes

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