Hydrochloric Acid → 11-Carboxyundecyl 5-amino-4-oxopentanoate hydrochloride
Reaction equation
[ClH:1].C(OCC)C.C([NH:14][CH2:15][C:16](=[O:36])[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:20])(OC(C)(C)C)=O>C(OCC)(=O)C>[ClH:1].[NH2:14][CH2:15][C:16](=[O:36])[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A 1.0 M solution of HCl in diethyl ether (5.0 mL; 5.0 mmol) was added to a stirred solution of the product of 14c (0.95 g; 2.2 mmol) in ethyl acetate (10 mL) at ambient temperature under argon. After 5 days, the mixture was filtered and the residue was triturated with diethyl ether (2×5 mL). The residue was dried overnight at 40° C. and 15 mm Hg to give 0.11 g white solid. The combined ether extracts were evaporated. LC-MS analysis indicated that the product contained ca. 25% 5-amino-4-oxopentanoic acid; the combined crops were purified by flash chromatography on a 150×25 mm silica gel 60 column eluted sequentially with 3% methanol in acetonitrile (1000 mL), 6% methanol in acetonitrile (1000 mL), then 9% methanol in acetonitrile (2000 mL), collecting 56×50 mL fractions. Fractions containing the product were evaporated and the residue was dissolved in water (10 mL). The solution was freeze-dried overnight, and 0.06 g (7.5%) product obtained (white solid, mp 110-115° C. (softens, no sharp mp)).
Workup
- filtrationthe mixture was filtered
- customthe residue was triturated with diethyl ether (2×5 mL)
- customThe residue was dried overnight at 40° C.
Sources & evidence
- ORD record
- ord-801e50831b014a2bbbafa8f41e5929b3
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249086B2
Reaction notes
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