Triphenylphosphine → 5-[(2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl)oxy]-1H-indole-1-carboxylic Acid 1,1-dimethylethyl Ester

HRID 1993714Notes

Reaction equation

HRID 1993714 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:51]([O:54][C@@H:55]1[C@@H:61]([O:62][C:63](=[O:65])[CH3:64])[C@H:60]([O:66][C:67](=[O:69])[CH3:68])[CH2:59][S:58][CH:56]1O)(=[O:53])[CH3:52]>C1COCC1>[CH3:3][C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH:56]3[S:58][CH2:59][C@@H:60]([O:66][C:67](=[O:69])[CH3:68])[C@H:61]([O:62][C:63](=[O:65])[CH3:64])[C@H:55]3[O:54][C:51](=[O:53])[CH3:52])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 150678682,3,4-tri-O-acetyl-5-thio-D-xylopyranoseHCID 22596220N-Boc-5-Hydroxyindole

Product 1

HCID 685418805-[(2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl)oxy]-1H-indole-1-carboxylic Acid 1,1-dimethylethyl EsterYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of 1.75 g (7.51 mM) of 5-hydroxy-1H-indole-1-carboxylic acid tert-butyl ester in 25 ml of THF, 2.73 g (13.5 mM) of diisopropylazodicarboxylate and 3.54 g (13.5 mM) of triphenylphosphine are added to a solution of 2.85 g (9.75 mM) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranose in 50 ml of THF. The reaction mixture is stirred at 45° C. for 3 hours and then concentrated under reduced pressure. The evaporation residue is dissolved in ethyl acetate and the organic phase is washed with a 1N solution of sodium hydroxide, and then with a concentrated aqueous solution of ammonium chloride. The organic phase is subsequently dried over magnesium sulfate and concentrated under reduced pressure. The evaporation residue is purified by C18-grafted silica chromatography, elution being carried out with an acetonitrile/water mixture (7/3; v/v). The desired product is obtained in the form of a pale yellow solid with a yield of 11%.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe evaporation residue is dissolved in ethyl acetate
  3. washthe organic phase is washed with a 1N solution of sodium hydroxide
  4. dry with materialThe organic phase is subsequently dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe evaporation residue is purified by C18-grafted silica chromatography, elution

Sources & evidence

ORD record
ord-f1dfbea6afa74001b9851a07e7842a12
Source dataset
uspto-grants-2010_01
Patent number
US07652032B2

Reaction notes

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