HCID 22007595, compound → HCID 22036085, compound

HRID 2306983Notes

Reaction equation

HRID 2306983 reaction equation
CCCCCCC.[CH3:8][CH:9]([OH:11])[CH3:10].[CH3:12][CH2:13][N:14](CC)[CH2:15][CH3:16]>CC(O)C.C1COCC1>[CH3:8][CH:9]([OH:11])[CH3:10].[NH:14]([CH2:15][CH3:16])[CH2:13][CH3:12]

Participants

3

Reactant 1

HCID 22007595HCID 22007595, compound

Product 1

HCID 22036085HCID 22036085, compound

Reagents, catalysts & solvents 1

HCID 22597222Tetrahydrofuran 2-propanolSolvent

Procedure

The racemate was resolved by chiral support chromatography. Portions of the racemate (0.2 g dissolved in 10 mL of 3:1 iPrOH/THF) were injected onto a preparative Chiralcel OD™ column equilibrated at 30° C. with 800:200:1 heptane/iPrOH/Et3N. Assignment of absolute configurations to the separated enantiomers was made by comparison of the CD spectra to those of the 10-chloro strictures. Analytical HPLC analysis (tR=17.2 min on a Chiralcel™ OD-H at a 0.5 mL min−1 flow rate of 800:200:1 hepane/iPrOH/Et2NH) gave an ee of 97%: UV λmax nm (ε, L.mol−1.cm−1) 284 (4740); CD λmax nm (θ, deg.cm2.dmol−1) 298 (3700), 273 (4400).

Sources & evidence

ORD record
ord-093b71acefee4b52a228c099f9c50a8c
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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