Triphenylphosphine → 6-[(2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranosyl)oxy]-1H-indole-1-carboxylic Acid, 1,1-dimethylethyl Ester

HRID 1993732노트

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HRID 1993732 반응식
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[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>[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][C@H:56]1[O:17][C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[CH:9][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[CH:12][CH:13]=1)(=[O:53])[CH3:52]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 150678682,3,4-tri-O-acetyl-5-thio-D-xylopyranoseHCID 24728908tert-Butyl 6-hydroxy-1H-indole-1-carboxylate

생성물 1

HCID 866301236-[(2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranosyl)oxy]-1H-indole-1-carboxylic Acid, 1,1-dimethylethyl Ester수율 3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
50 °C

실험 절차

A solution of 2.66 g (11.41 mM) of 6-hydroxy-1H-indole-1-carboxylic acid tert-butyl ester in 50 ml of THF, 4.16 g (20.6 mM) of diisopropylazodicarboxylate and 5.39 g (20.6 mM) of triphenylphosphine are added to a solution of 4.34 g (14.84 mM) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranose in 150 ml of THF. The reaction mixture is stirred at 50° C. for 4 hours and then concentrated under reduced pressure. The evaporation residue is solubilized 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 silica gel chromatography, elution being carried out with a methylcyclohexane/ethyl acetate mixture (gradient of 9/1 to 7/3; v/v). The residue obtained is subsequently purified by C18-grafted silica chromatography, elution being carried out with an acetonitrile/water mixture (6/4; v/v). The desired product is obtained in the form of a white solid with a yield of 3%.

후처리

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

출처 및 근거

ORD 기록
ord-cbbbead4d6da43a09b0fdfcb11960157
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652032B2

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