Hydrochloric Acid → HCID 131728761, compound

HRID 604768Notes

Reaction equation

HRID 604768 reaction equation
C(OC(=O)[N:7]([CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH2:32][CH2:33][CH2:34][CH2:35][NH:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH:53]=[CH:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])=[C:40]([O:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH:72]=[CH:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH3:81])[CH:39]=1)C(OC(C)(C)C)=O)[CH2:8][CH2:9][CH2:10][CH2:11][NH:12]C(OC(C)(C)C)=O)(C)(C)C.[ClH:83]>C(OCC)(=O)C>[ClH:83].[ClH:83].[ClH:83].[ClH:83].[NH2:12][CH2:11][CH2:10][CH2:9][CH2:8][NH:7][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:32][CH2:33][CH2:34][CH2:35][NH:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH:53]=[CH:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])=[C:40]([O:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH:72]=[CH:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH3:81])[CH:39]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 123981859HCID 123981859, compound

Product 1

HCID 131728761HCID 131728761, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

A concentrated solution of the amine 19 (0.253 g, 0.22 mmol) in ethyl acetate was added cooled to 0° C. A total of 5 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 during which time a white precipitate formed. The ethyl acetate was removed in vacuo and the residue co-evaporated with ethyl acetate and chloroform to give the product 26 as a white powder (0.215 g, 98%); 1H NMR (CD3OD) δ 7.13 (s, 1H, aryl), 7.04 (d, 1H, aryl), 6.98 (d, 1H, aryl), 5.33 (t, 4H, olefinic), 4.12 (m, 2H, benzylic), 4.03 (t, 2H, OCH2), 3.99 (t, 2H, OCH2), 3.08 (m, 10H, 5×CH2), 2.98 (t, 2H, CH2), 2.02 (m, 8H, CH2C═C), 1.89 (m, 16H, 8×CH2), 1.47 (m, 4H, 2×CH2), 1.42-1.19 (m, 40H, 20×CH2), 0.89 (t, 6H, CH3); 13C NMR (300 MHz, D2O) δ 149.74, 148.90, 129.62, 129.46, 123.92, 123.71, 69.36, 68.88, 51.12, 46.68, 38.99, 32.14, 29.97, 29.81, 29.60, 27.36, 26.53, 24.69, 24.22, 23.14, 23.06, 22.84, 14.05; HRMS (FAB): theory for C55H105N4O2 (M+1), 853.8238; found (M+1), 853.8264; Anal. (C55H109Cl4N4O2.0.6H2O): C, H, N.

Workup

  1. customformed
  2. customThe ethyl acetate was removed in vacuo

Sources & evidence

ORD record
ord-cfb33db512b6462bb4a625ddb188a1bf
Source dataset
uspto-grants-2011_03
Patent number
US07910363B1

Reaction notes

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