Triethylamine → N-6-bromohexanoyl-L-leucine ethyl ester

HRID 864465Notes

Reaction equation

HRID 864465 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:12])[C@H:6]([CH2:8][CH:9]([CH3:11])[CH3:10])[NH2:7])[CH3:3].C(N(CC)CC)C.[Br:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27]>C1COCC1.[Cl-].[NH4+].C(OCC)(=O)C>[CH2:2]([O:4][C:5](=[O:12])[C@H:6]([CH2:8][CH:9]([CH3:11])[CH3:10])[NH:7][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][Br:20])[CH3:3]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 898486-Bromohexanoyl chlorideHCID 11658447L-Leucine, ethyl ester, hydrochloride (1:1)

Product 1

HCID 22866411N-6-bromohexanoyl-L-leucine ethyl esterYield 80%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A stirred suspension of L-leucine ethyl ester hydrochloride (8.38 g, 45 mmol) in dry THF (80 ml) at room temperature was treated with triethylamine (6.3 ml, 45 mmol). The reaction mixture was treated with 6-bromohexanoyl chloride (6.91 ml, 45 mmol). The reaction mixture was stirred for 4 h at room temperature and then diluted with a mixture of saturated aqueous ammonium chloride and ethyl acetate. The organic layer was separated, washed with saturated aqueous ammonium chloride, dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to give N-6-bromohexanoyl-L-leucine ethyl ester (12.1 g, 80%) as an oil which was used for the next step without further purification.

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous ammonium chloride
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-825b0c937ac6420892ded97bbd91ba54
Source dataset
uspto-grants-1996_10
Patent number
US05563151

Reaction notes

Loading…