Hydrochloric Acid → HCID 131728763, compound

HRID 604770Notes

Reaction equation

HRID 604770 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][C:37](=[O:82])[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:84]>C(OCC)(=O)C>[ClH:84].[ClH:84].[ClH:84].[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][C:37](=[O:82])[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 123361765HCID 123361765, compound

Product 1

HCID 131728763HCID 131728763, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

A concentrated solution of the amide 21 (0.22 g, 0.19 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 28 as a white powder (0.18 g, 98%); 1H NMR (CDCl3/CH3OD 9:1) d 7.42 (m, 2H, aryl), 6.78 (m, 1H, aryl), 5.33 (m, 4H, olefinic), 4.03 (m, 4H, OCH2), 3.41 (m, 2H, CH2), 3.01 (m, 10H, 5×CH2), 2.08-1.66 (m, 24H, 12×CH2), 1.71 (m, 6H, 3×CH2), 1.56-1.13 (m, 44H, 20×CH2), 0.89 (t, 6H, CH3); HRMS (FAB): theory for C55H105N4O3 (M+1), 867.8025; found (M+1), 867.8022; Anal. Calcd for (C55H105Cl3N4O3.1.5H2O): C, H, N.

Workup

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

Sources & evidence

ORD record
ord-e848f9d1751d4c98b79eab5e0fd7b97d
Source dataset
uspto-grants-2011_03
Patent number
US07910363B1

Reaction notes

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