6-Aminohexanoic Acid → HCID 86751508, compound

HRID 2293014Notes

Reaction equation

HRID 2293014 reaction equation
O=[C:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:3][CH2:4][CH:5]=O.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]C(O)=O.[CH3:21][OH:22].[OH2:23]>>[CH2:7]([C:2]1[N:12]([CH:13]([CH2:14][CH2:15][CH2:16][CH3:17])[C:21]([OH:23])=[O:22])[CH:5]=[CH:4][CH:3]=1)[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 3

HCID 5646-Aminohexanoic AcidHCID 1562884-Oxononan-1-alHCID 22242641Methanol--water (1/1)

Product 1

HCID 86751508HCID 86751508, compoundYield 11%

Procedure

Structure 8a was prepared according to the method described by E. DiFranco et al., Chem. Res. Toxicol. 8: 61-67 (1995). The procedure was approximately as follows: 4-oxononanal (50 mg, 0.320 mmol) and 6-aminocaproic acid (50 mg, 0.384 mmol) in MeOH/H2O (500 μL, 19:1 v:v) were stirred for 16 h at room temperature. Solvents were then removed into a dry ice-cooled trap using high vacuum. EtOAc (1 mL) was added and the solution was filtered. The crude product was then purified by HPLC using 55% EtOAc/hexanes as eluant to obtain structure 8a (approximately 11 mg, 11%) as a tan solid.

Workup

  1. customStructure 8a was prepared
  2. customSolvents were then removed into a dry ice-
  3. temperaturecooled trap
  4. additionEtOAc (1 mL) was added
  5. filtrationthe solution was filtered
  6. customThe crude product was then purified by HPLC

Sources & evidence

ORD record
ord-b66cd26db4ad48f7af55f7e891da0f32
Source dataset
uspto-grants-1997_11
Patent number
US05686250

Reaction notes

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