1,4-Dioxane → 71347-90-5

HRID 1416519Notes

Reaction equation

HRID 1416519 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C@:15]12([CH2:25]S(O)(=O)=O)C(C)(C)[CH:19]([CH2:20][CH2:21]1)[CH2:18][C:16]2=O.[CH3:30][C:31]#[N:32].[OH2:33].[O:34]1[CH2:39]COCC1>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][O:14][CH2:30][CH2:31][NH:32][C:39]([O:34][CH2:25][C:15]1[CH:16]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:33])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 280458benzyl N-(2-hydroxyethyl)carbamateHCID 18373917Acetonitrile--water (1/1)

Product 1

HCID 309084971347-90-5

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 300 mg (80% purity, 0.271 mmol) of the 6-octyloxy-2-naphthoyl starting material above prepared, 1.4 grams (7.18 mmol) of 2-(N-benzyloxycarbonylamino)ethanol and 62.9 mg (0.271 mmol) of (1S)-(+)-10-camphorsulfonic acid in 10 ml anhydrous dioxane and 1 mL anhydrous DMF was stirred at 25° C. HPLC analysis using 65% CH3CN/H2O at 1.5 mL/min with detection at 210 and 277 nm indicated. after 18 hours a greater than 95 percent conversion to a less polar product (tR =3.36 min). The reaction was quenched with 1M NaHC03, the reaction mixture diluted with water and subjected to reverse-phase flash chromatography eluting with 40-60 percent CH3CN/H2O in 10% step gradients to obtain after lyophilization of the 60 percent fractions, ether ##STR10##

Workup

  1. customThe reaction was quenched with 1M NaHC03
  2. additionthe reaction mixture diluted with water
  3. washeluting with 40-60 percent CH3CN/H2O in 10% step gradients
  4. customto obtain after lyophilization of the 60 percent fractions, ether

Sources & evidence

ORD record
ord-9bb735c85cb3464ab306aae4b8c9764c
Source dataset
uspto-grants-1999_06
Patent number
US05914313

Reaction notes

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