Hydrochloric Acid → HCID 131728759, compound

HRID 604766Notes

Reaction equation

HRID 604766 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:34]=[CH:35][C:36]=1[O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH:46]=[CH:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:23][NH:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][NH2:33])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[ClH:56]>C(OCC)(=O)C>[ClH:56].[ClH:56].[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:34]=[CH:35][C:36]=1[O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH:46]=[CH:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:23][NH:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][NH2:33])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70040444HCID 70040444, compound

Product 1

HCID 131728759HCID 131728759, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

A concentrated solution of the amine 17 (0.14 g, 0.18 mmol) in ethyl acetate was added cooled to 0° C. A total of 4 mL of a freshly prepared saturated solution of HCl in ethyl acetate was added dropwise and the solution stirred for 1 h at room temperature. The ethyl acetate was removed in vacuo and the residue co-evaporated with ethyl acetate and chloroform to give the product 24 as an off white powder (0.15 g, 98%); 1H NMR (CDCl3) d 7.27 (s, 1H, aryl), 7.00 (d, 1H, aryl), 6.82 (d, 1H, aryl), 5.33 (m, 4H, olefinic), 4.14 (m, 2H, benzylic), 4.01 (t, 2H, OCH2), 3.95 (t, 2H, OCH2), 3.87 (t, 2H, CH2), 3.78 (t, 2H, CH2), 3.70 (t, 4H, CH2), 3.25 (t, 2H, CH2) 2.93 (m, 2H, CH2), 2.02 (m, 8H, CH2C═C), 1.89 (m, 4H, CH2CH2O), 1.53-1.18 (m, 44H, 22×CH2), 0.89 (t, 6H, CH3); 13C NMR (300 MHz, CDCl3) d 149.91, 149.62, 130.12, 130.00, 123.28, 122.61, 115.46, 113.63, 70.22, 70.09, 69.64, 69.40, 66.50, 65.98, 51.06, 45.08, 40.11, 32.28, 30.15, 29.92, 29.70, 27.60, 26.54, 26.43, 23.07, 14.54; HRMS (FAB): theory for C49H91N2O4 (M+1), 771.6973; found (M+1), 771.6967; Anal. (C49H92Cl2N2O4.0.4H2O): C, H, N.

Workup

  1. customThe ethyl acetate was removed in vacuo

Sources & evidence

ORD record
ord-7775bc12ce1544648ae31b8d40d152f5
Source dataset
uspto-grants-2011_03
Patent number
US07910363B1

Reaction notes

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