Triethylamine → HCID 178462020, compound

HRID 1806724Notes

Reaction equation

HRID 1806724 reaction equation
Cl.[C:2]([O:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH2:9])([CH3:5])([CH3:4])[CH3:3].[O-]S([O-])(=O)=O.[Mg+2].C(N(CC)CC)C.[CH3:25][C:26]([CH3:31])([CH3:30])[CH2:27][CH:28]=O>C(Cl)Cl>[C:2]([O:6][C:7](=[O:11])[C@@H:8](/[N:9]=[CH:28]/[CH2:27][C:26]([CH3:31])([CH3:30])[CH3:25])[CH3:10])([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 763353,3-DimethylbutanalHCID 11275390tert-Butyl alaninate hydrochloride

Product 1

HCID 178462020HCID 178462020, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of L-alanine tert-butyl ester hydrochloride (Bachem) (1.8 g, 10 mmol) and MgSO4 in CH2Cl2 (100 mL) was added triethylamine (1.5 g, 15 mmol). The mixture was stirred at room temperature for 1 h, and 3,3-dimethyl-butyraldehyde (1 g, 10 mmol) was added. The reaction mixture was stirred at room temperature for 18 h. The mixture was filtered, and the filtrate was washed with water, brine, and concentrated. The residue was dried under reduced pressure to give (S)-2-[3,3-dimethyl-but-(E)-ylideneamino]-propionic acid tert-butyl ester as colorless oil (2.3 g, 100%) which was used without further purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. filtrationThe mixture was filtered
  3. washthe filtrate was washed with water, brine
  4. concentrationconcentrated
  5. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-f40bad915ad44f298c57993a44c13266
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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