Hydrogen Bromide → Carboxymethyl 5-amino-4-oxopentanoate hydrobromide

HRID 1771024Notes

Reaction equation

HRID 1771024 reaction equation
[BrH:1].C([NH:9][CH2:10][C:11](=[O:25])[CH2:12][CH2:13][C:14]([O:16][CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])=[O:15])(OC(C)(C)C)=O>C(O)(=O)C>[BrH:1].[NH2:9][CH2:10][C:11](=[O:25])[CH2:12][CH2:13][C:14]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 90034544t-butoxycarbonylmethyl 5-(Boc-amino)-4-oxopentanoate

Product 1

HCID 90034574Carboxymethyl 5-amino-4-oxopentanoate hydrobromideYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 30% solution of hydrogen bromide in acetic acid (12 mL) was added to the product of 1a (3.3 g; 9.5 mmol) cooled with an ice-water bath and stirred until the oil dissolved with evolution of gas. After stirring for 15 min, the mixture was triturated with hexane (4×20 mL) and 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 12 mm Hg. 4.44 g (92%) product was obtained (tan powder, mp 110-114° C. (dec.)).

Workup

  1. temperaturecooled with an ice-water bath
  2. dissolutiondissolved with evolution of gas
  3. stirringAfter stirring for 15 min
  4. customthe mixture was triturated with hexane (4×20 mL) and diethyl ether (4×20 mL)
  5. filtrationThe residue was filtered
  6. customdried overnight in a drying pistol at ˜50° C.

Sources & evidence

ORD record
ord-e967cac021ed444685766933b4fc5d22
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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