Acetic Acid → HCID 68865763, compound
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:18][CH2:17][CH:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][C:8]=2[S:9][C:10]=1[NH:11][C:12](=[O:14])[CH3:13])=[O:5])[CH3:2].CC(O)=[O:28]>O>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:18][CH2:17][CH:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:15](=[O:28])[C:8]=2[S:9][C:10]=1[NH:11][C:12](=[O:14])[CH3:13])=[O:5])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
Compound 02-3 (22.1 g, 62 mmol) was dissolved in AcOH (200 mL). The mixture was heated to 65° C. and a solution of Na2Cr2O7-2H2O (27.2 g, 93 mmol) in hot H2O (200 mL) was added over a period of 2 min. After complete addition the mixture was stirred for 3 h at 65-67° C. and 2 h at 75° C. The mixture was allowed to cool to RT and then quenched with saturated aqueous Na2SO3 (100 mL) and diluted with H2O (1.5 L). The aqueous mixture was extracted with EtOAc (3×300 mL). The combined organic layers were washed with H2O (3×400 mL), brine (400 mL) and dried over Na2SO4. After removal of the solvent in vacuo the crude product was treated with Et2O (50 mL) and filtered off to give 02-4 (9.5 g, 25 mmol, 41%) as yellow powder containing about 8% of starting material 02-3 (HPLC).
Workup
- additionAfter complete addition the mixture
- temperatureto cool to RT
- customquenched with saturated aqueous Na2SO3 (100 mL)
- additiondiluted with H2O (1.5 L)
- extractionThe aqueous mixture was extracted with EtOAc (3×300 mL)
- washThe combined organic layers were washed with H2O (3×400 mL), brine (400 mL)
- dry with materialdried over Na2SO4
- customAfter removal of the solvent in vacuo the crude product
- additionwas treated with Et2O (50 mL)
- filtrationfiltered off
Sources & evidence
- ORD record
- ord-3dbf4b53bfc243ee8c3837cb431c0a06
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07524853B2
Reaction notes
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