Hydrochloric Acid → 3-[4-(2-Octadec-9-enyloxycarbonyl-ethylamino)-butylamino]-propionic acid octadec-9-enyl ester bis hydrochloride salt

HRID 31538Notes

Reaction equation

HRID 31538 reaction equation
[CH2:1]([O:19][C:20](=[O:66])[CH2:21][CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][CH2:25][CH2:26][CH2:27][N:28](C(OC(C)(C)C)=O)[CH2:29][CH2:30][C:31]([O: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][CH2:50][CH3:51])=[O:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[ClH:67]>C(Cl)Cl.CCOC(C)=O>[ClH:67].[ClH:67].[CH2:1]([O:19][C:20](=[O:66])[CH2:21][CH2:22][NH:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH:42]=[CH:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])=[O:32])[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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 866188503-(tert-Butoxycarbonyl-{4-[tert-butoxycarbonyl-(2-octadec-8-enyloxycarbonyl-ethyl)-amino]-butyl}-amino)-propionic acid octadec-8-enyl ester

Product 1

HCID 866188523-[4-(2-Octadec-9-enyloxycarbonyl-ethylamino)-butylamino]-propionic acid octadec-9-enyl ester bis hydrochloride saltYield 91%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The ester 5 (n=4, R=oleyl; 13.0 g, 13.9 mmol) was dissolved in CH2Cl2 (70 mL) and treated with 4M HCl in EtOAc (140 mL). The resulting mixture was stirred at rt. for 2 h, then the solvent was removed in vacuo and the residue was triturated with anhydrous diethyl ether (150 mL) to afford a solid which was dried in vacuo to afford bis hydrochloride 6 as a white powder (10.23 g, 91%).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was triturated with anhydrous diethyl ether (150 mL)
  3. customto afford a solid which
  4. customwas dried in vacuo

Sources & evidence

ORD record
ord-5c0dc01d4cb24c88a62d0995d1782164
Source dataset
uspto-grants-2008_09
Patent number
US07425645B2

Reaction notes

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