D-alpha-Amino-epsilon-caprolactam Chemical Properties

Melting point:

97-101 °C

Boiling point:

315.1±35.0 °C(Predicted)

Density 

1.031±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,PBS (pH 7.2): 10 mg/ml

form 

A neat oil

pka

16.06±0.40(Predicted)

InChI

InChI=1S/C6H12N2O/c7-5-3-1-2-4-8-6(5)9/h5H,1-4,7H2,(H,8,9)/t5-/m1/s1

InChIKey

BOWUOGIPSRVRSJ-RXMQYKEDSA-N

SMILES

N1CCCC[C@@H](N)C1=O

Safety Information

RIDADR 

1759

HazardClass 

8

PackingGroup 

III

D-alpha-Amino-epsilon-caprolactam Usage And Synthesis

Uses

(S)-3-Amino-2-azepanone is a useful research chemical. It is used as an intermediate in the synthesis of bengamide E analogs and capuramycin and its analogs as antibacterial agents. (R)-3-Amino-2-azepanone is used as an intermediate for the synthesis of β-oxocarboxamides as antiviral agents.

Definition

ChEBI: D-2-aminohexano-6-lactam is a 2-aminohexano-6-lactam. It is a conjugate base of a D-2-ammoniohexano-6-lactam. It is an enantiomer of a L-2-aminohexano-6-lactam.

Synthesis

General procedure for the synthesis of (R)-3-amino-2-caprolactam from L-lysine hydrochloride: 30 g (164 mmol) of L-lysine hydrochloride and 150 mL of 1,2-propanediol as a solvent were added to a 250 mL three-neck flask. Under stirring conditions, 6.57 g of sodium hydroxide was slowly added with continuous stirring until complete dissolution. Subsequently, the reaction mixture was heated to reflux and the reflux reaction was maintained for 5 hours, during which time the water generated was removed by means of a water separator and the progress of the reaction was monitored by thin-layer chromatography (TLC) until the reaction was complete. Upon completion of the reaction, the mixture was cooled to room temperature and the by-product sodium chloride was removed by filtration. The filtrate was acidified dropwise by adding 6 mol/L aqueous hydrochloric acid to the filtrate, followed by a back-extraction operation. The aqueous phase was collected, dried over anhydrous sodium sulfate, and recrystallized by adding appropriate amount of ethanol to finally obtain 21.9 g of white solid product (R)-α-amino caprolactam in 81% yield.

References

[1] Patent: CN106946779, 2017, A. Location in patent: Paragraph 0031; 0033; 0034

D-alpha-Amino-epsilon-caprolactam(28957-33-7)Related Product Information

• 1-2-(2,4-difluorophenyl)-2-propenol acetate
• Pyrazinecarboxylic acid, 5-methyl-, 1-oxide (9CI)
• (R)-3-AMINOAZEPAN-2-ONE HYDROCHLORIDE
• 3-Amino-2-azepanone
• 4-Methoxyphenethylamine
• 5-broMo-2-chloro-N-cyclopentylpyriMidin-4-aMine
• 2-(2,4-Difluorophenyl)-2-propenyl-propanedioic Acid Diethyl Ester
• 2-Acetyloxy-1(2,4-difluorophenyl)ethanone
• 2,3-DIMETHOXYPHENETHYLAMINE
• 3-Methoxyphenethylamine
• 3-(3,4-DIMETHOXY-PHENYL)-PROPYLAMINE
• 3,4,5-Trimethoxyphenylacetonitrile
• 5-(Chloromethyl)-1,2,3-trimethoxybenzene
• 10-Hydroxy Warfarin β-D-Glucuronide
• Benzeneacetic acid, 2,4,5-triMethoxy-
• D-alpha-Amino-epsilon-caprolactam
• (R)-3-(BOC-AMINO)-2-OXO-1-AZEPINE-ACETIC ACID
• (D)-N-(HEXAHYDRO-(1H)-AZEPIN-2-ON-3-YL)INDOLE-6-CARBOXAMIDE