Hydrochloric Acid → HCID 131728762, compound

HRID 604769Notes

Reaction equation

HRID 604769 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:70])[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[C:28]([O:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH:60]=[CH:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH3:69])[CH:27]=1)C(OC(C)(C)C)=O)(C)(C)C.[ClH:72]>C(OCC)(=O)C>[ClH:72].[ClH:72].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:70])[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[C:28]([O:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH:60]=[CH:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH3:69])[CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 123227557HCID 123227557, compound

Product 1

HCID 131728762HCID 131728762, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

A concentrated solution the amide 20 (0.22 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 27 as a white powder (0.19 g, 98%); 1H NMR (CDCl3) d 8.95 (br s, 2H, R2N+H2), 8.20 (br s, 3H, RN+H3), 7.45 (m, 2H, aryl), 6.78 (m, 1H, aryl), 5.33 (m, 4H, olefinic), 3.95 (m, 4H, OCH2), 3.38 (m, 2H, CH2), 3.11 (m, 2H, CH2), 3.01 (m, 4H, 2×CH2), 2.08-1.89 (m, 14H, 7×CH2), 1.71 (m, 6H, 3×CH2), 1.47-1.18 (m, 44H, 20×CH2), 0.89 (t, 6H, CH3); HRMS (FAB): theory for C51H94N3O3 (M+1), 796.7290; found (M+1), 796.7249; Anal. (C51H95Cl2N3O3.1.6H2O): C, H, N.

Workup

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

Sources & evidence

ORD record
ord-d9792b13255d41009c2b09800965253f
Source dataset
uspto-grants-2011_03
Patent number
US07910363B1

Reaction notes

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