HCID 22452562, compound → HCID 22452564, compound

HRID 2185917Notes

Reaction equation

HRID 2185917 reaction equation
C([C:4]1[O:5][C:6]2[C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:7]=2[C:8](=O)[C:9]=1[CH3:10])(=O)C.[CH3:19][C:20]([CH3:41])([O:22][C:23]([NH:25]C1OC2C(C=CC)=CC=CC=2C(=O)C=1C)=[O:24])[CH3:21]>>[C:16]([C:15]1[C:6]2[O:5][C:4]([NH:25][C:23]([O:22][C:20]([CH3:41])([CH3:21])[CH3:19])=[O:24])=[C:9]([CH3:10])[CH2:8][C:7]=2[CH:12]=[CH:13][CH:14]=1)([OH:18])=[O:17]

Participants

3

Reactant 2

HCID 22452562HCID 22452562, compoundHCID 69971980HCID 69971980, compound

Product 1

HCID 22452564HCID 22452564, compound

Procedure

The title compound was synthesised following the procedure described for Compound 2C, except that Compound 3A was used instead of Compound 2B. The reaction was carried out at 40° C. Treatment of the reaction mixture with sodium dithionite and extraction with chloroform afforded a crude which was rinsed with 50 mL of ethyl acetate, boiled for 2 hours and filtered to give a first crop of Compound 3B. The mother liquor was evaporated and the residue was purified by flash chromatography (ethyl acetate/petroleum ether/glacial acetic acid 50:50:1) to give a second crop of Compound 3B. Total yield: 34%.

Workup

  1. customThe title compound was synthesised
  2. customwas carried out at 40° C
  3. extractionTreatment of the reaction mixture with sodium dithionite and extraction with chloroform
  4. customafforded a crude which
  5. washwas rinsed with 50 mL of ethyl acetate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-27652626303843a098a7a575d75226cc
Source dataset
uspto-grants-2002_06
Patent number
US06403594B1

Reaction notes

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