Acetic Acid → HCID 69907482, compound

HRID 618132Notes

Reaction equation

HRID 618132 reaction equation
[C:1]([CH2:4][S:5]/[C:6](=[CH:21]\[C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)/[C:7]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=1)=[O:8])([OH:3])=[O:2].[CH3:31][Si](C=[N+]=[N-])(C)C.C(O)(=O)C>C(Cl)(Cl)Cl.CO.CCCCCC>[NH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22](/[CH:21]=[C:6](\[S:5][CH2:4][C:1]([O:3][CH3:31])=[O:2])/[C:7]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)=[O:8])=[CH:23]1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 69907607HCID 69907607, compound

Product 1

HCID 69907482HCID 69907482, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 8058HexaneSolvent

Procedure

Compound 107 (50.0 mg) obtained in Example 107 was dissolved in a mixed solvent of chloroform (10 ml) and methanol (5 ml), and a solution (0.5 ml) of trimethylsilyldiazomethane in hexane, followed by stirring for 10 minutes. Acetic acid (20.0 mg) was added to the reaction solution and the mixture was subjected to partitioning between chloroform and a 5% aqueous solution of sodium bicarbonate. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from isopropyl ether to give Compound 108 (36.9 mg).

Workup

  1. customto partitioning between chloroform
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography
  4. customThe obtained crude crystals
  5. customwere recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-edb56248339e411a8cb1935876415255
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Reaction notes

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