Dimethylamine → HCID 58473243, compound

HRID 713838Notes

Reaction equation

HRID 713838 reaction equation
[CH2:1]([C:19]1([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]/[CH:38]=[CH:39]\[CH2:40]/[CH:41]=[CH:42]\[CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[O:24][CH2:23][CH:22]([CH2:25]S(C)(=O)=O)[CH2:21][O:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:48][NH:49][CH3:50]>C1COCC1.CO.C(Cl)(Cl)Cl>[CH2:1]([C:19]1([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]/[CH:38]=[CH:39]\[CH2:40]/[CH:41]=[CH:42]\[CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[O:24][CH2:23][CH:22]([CH2:25][N:49]([CH3:50])[CH3:48])[CH2:21][O:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 2

HCID 674DimethylamineHCID 131734056HCID 131734056, compound

Product 1

HCID 58473243HCID 58473243, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the above crude material (VII, 1.0 g) under nitrogen was added 20 mL of dimethylamine in THF (2.0 M). The resulting mixture was stirred at room temperature for 7 days. An oily residual was obtained upon evaporation of the solvent. Column chromatography on silica gel (230-400 mesh, 100 mL) with 0-3% methanol gradient in chloroform as eluent resulted in 150 mg of the product DLin-K6S-C1-DMA as pale oil. 1H NMR (400 MHz, CDCl3) δ: 5.24-5.51 (8, m, 4×CH═CH), 4.04 (2H, dd, 2×OCH)), 3.75 (2H, dd OCH), 2.7-2.9 (2H, br, NCH2), 2.78 (4H, t, 2×C═C—CH2—C═C), 2.57 (6H, s, 2×NCH3), 1.95-2.17 (9H, q, 4× allylic CH2 and CH), 1.67-1.95 (2H, m, CH2), 1.54-1.65 (4H, m, 2×CH2), 1.22-1.45 (32H, m), 0.90 (6H, t, 2×CH3) ppm.

Workup

  1. customAn oily residual was obtained upon evaporation of the solvent

Sources & evidence

ORD record
ord-0d14750bdbb1451fb859b0053858cf43
Source dataset
uspto-grants-2015_11
Patent number
US09186325B2

Reaction notes

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