Pyridine → HCID 10503558, compound

HRID 363504Notes

Reaction equation

HRID 363504 reaction equation
[CH2:1]([O:8][CH2:9][C@:10]1([CH2:16][OH:17])[O:14][C:13](=[O:15])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.CN(C1C=CC=CN=1)C.[C:33](Cl)(=[O:47])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]>C(Cl)Cl>[CH2:1]([O:8][CH2:9][C@:10]1([CH2:16][O:17][C:33](=[O:47])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[O:14][C:13](=[O:15])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 218852-DimethylaminopyridineHCID 66986Myristoyl chlorideHCID 10752281HCID 10752281, compound

Product 1

HCID 10503558HCID 10503558, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.14 (0.024 g, 0.1 mmol) in CH2Cl2 (5 mL) was stirred with pyridine (0.032 mL, 0.4 mmol), a catalytic amount of dimethylaminopyridine, and tetradecanoyl chloride (0.054 mL, 0.2 mmol) for 2 h at room temperature. The solution was concentrated and the residue was purified by flash column chromatography over silica gel with hexane:EtOAc (2:1) as eluant to give 2.15 (0.041 g, 92%) as an oil; [α]22D +1.43° (c 4.2, CHCl3); IR (neat) 1783 and 1743 cm-1 (C=O); 1H NMR (CDCl3) δ 0.85 (distorted triplet, 3 H, CH3), 1.10-1.40 (m, 20 H, CH3 (CH2)10CH2CH2CO), 1.60 (br m, 2 H, CH3 (CH2)10CH2CH2CO), 2.00-2.30 (m, 2 H, H-4), 2.30 (t, J=7.5 Hz, 2 H, CH3 (CH2)10CH2CH2CO), 2.50-2.75 (m, 2 H, H-3), 3.60 (br s, 2 H, CH2OCH2Ph), 4.20 (AB q, J=11.9 Hz, 2 H, CH2OCO), 4.55 (br s, 2 H, CH2OCH2Ph), 7.20-7.40 (m, 5 H, Ph); 13C NMR (CDCl3) δ 14.09, 22.65, 24.81, 26.40, 28.78, 29.07, 29.20, 29.32, 29.42, 29.57, 29.61, 29.64, 31.89, 34.03, 65.99, 72.21, 73.76, 84.94, 127.63, 127.93, 128.49, 137.33, 173.14, 176.30. Anal. Calcd for C27H42O5 : C, 72.61; H, 9.48. Found: C, 72.70; H, 9.50.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by flash column chromatography over silica gel with hexane:EtOAc (2:1) as eluant

Sources & evidence

ORD record
ord-21c115155dd54fad9f577cf51db50035
Source dataset
uspto-grants-1999_02
Patent number
US05874464

Reaction notes

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