Acetic Acid → HCID 54206313, compound

HRID 1417477Notes

Reaction equation

HRID 1417477 reaction equation
[N+:1](=C)=[N-].[CH2:4]([N:11]1[C:23]2[C:22]([S:24][CH3:25])=[C:21]([CH2:26][C:27]([OH:29])=O)[CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(O)(=O)C>C(OCC)C>[CH2:4]([N:11]1[C:23]2[C:22]([S:24][CH3:25])=[C:21]([CH2:26][C:27]([NH2:1])=[O:29])[CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 9906964HCID 9906964, compound

Product 1

HCID 54206313HCID 54206313, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

An excess of a solution of diazomethane in diethyl ether was added to a solution of 150 mg of 9-benzyl-1-methylthiocarbazol-2-acetic acid, as obtained in Example 5, in 3 ml of diethyl ether. The resulting reaction mixture was stirred for 10 minutes at room temperature and then glacial acetic acid was added. The reaction mixture was next concentrated by evaporation under reduced pressure. 10 ml of saturated methanolic ammonia was added to a solution of the resulting residue in 5 ml of methanol, and the reaction mixture was stirred for 7 days at room temperature. After this time, the reaction mixture was concentrated by evaporation under reduced pressure and the resulting residue was subjected to column chromatography using 400 mg of silica gel using, as eluent, a 4:1 by volume mixture of hexane and ethyl acetate to yield 131 mg of the title compound as an amorphous solid.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was next concentrated by evaporation under reduced pressure
  3. addition10 ml of saturated methanolic ammonia was added to a solution of the resulting residue in 5 ml of methanol
  4. stirringthe reaction mixture was stirred for 7 days at room temperature
  5. concentrationAfter this time, the reaction mixture was concentrated by evaporation under reduced pressure
  6. additionas eluent, a 4:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-e7ba9c7bb02b4de088ff70c0753219d3
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

Loading…