Hydrochloric Acid → Carboxymethyl 5-amino-4-oxopentanoate hydrochloride

HRID 1771023Notes

Reaction equation

HRID 1771023 reaction equation
[ClH:1].O1CCOCC1.C([NH:15][CH2:16][C:17](=[O:31])[CH2:18][CH2:19][C:20]([O:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[O:21])(OC(C)(C)C)=O>>[ClH:1].[NH2:15][CH2:16][C:17](=[O:31])[CH2:18][CH2:19][C:20]([O:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 90034544t-butoxycarbonylmethyl 5-(Boc-amino)-4-oxopentanoate

Product 1

HCID 90034553Carboxymethyl 5-amino-4-oxopentanoate hydrochlorideYield 96%

Procedure

A 4 M solution of hydrogen chloride in dioxane (35 mL; 0.14 mol) was added to the product of 1a (3.3 g; 9.5 mmol) and stirred until the oil dissolved with evolution of gas. After standing one hour, the solvent was evaporated and the residue was triturated with diethyl ether (4×20 mL); the oil solidified to a tan powder. The residue was filtered and dried overnight in a drying pistol at 50° C. and 13 mm Hg. 2.05 g (96%) product was obtained (tan powder).

Workup

  1. dissolutiondissolved with evolution of gas
  2. customthe solvent was evaporated
  3. customthe residue was triturated with diethyl ether (4×20 mL)
  4. filtrationThe residue was filtered
  5. customdried overnight in a drying pistol at 50° C.

Sources & evidence

ORD record
ord-c254d117cee048a8b71e32577e7e3de5
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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