Water → HCID 59432155, compound

HRID 506484Notes

Reaction equation

HRID 506484 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH:9]([CH:14]=[CH2:15])[C:10]([O:12][CH3:13])=[O:11])=[O:7])=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=1.C[N+]1([O-])CCOCC1.S([O-])([O-])=O.[Na+].[Na+].[OH2:36].C(O)(C)(C)C.[OH2:42]>C(O)(C)(C)C.O=[Os](=O)(=O)=O.C(OCC)(=O)C>[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH:9]([CH:14]([OH:42])[CH2:15][OH:36])[C:10]([O:12][CH3:13])=[O:11])=[O:7])=[C:4]([C:18]([F:19])([F:20])[F:21])[CH:3]=1

Participants

9

Reactant 5

HCID 962WaterHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 59432156HCID 59432156, compoundHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 59432155HCID 59432155, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

460 mg (1.5 mmol) of methyl 2-(4-fluoro-2-trifluoromethylbenzoylamino)but-3-enoate were dissolved in tert-butanol/water, and 360 mg (3 mmol) of N-methylmorpholine N-oxide and 1.5 g (0.15 mmol) of a 2.5% strength solution of OsO4 in tert-butanol were added. The mixture was stirred at RT for 60 hours. 3.2 g of sodium sulfite, water and ethyl acetate were then added, and the phases were separated. The aqueous phase was reextracted with ethyl acetate. The combined organic phases were washed and dried, and the solvent was removed. This gave 440 mg (86% of theory) of crude product (diastereomer ratio about 2:1) which was used for the next step without further purification.

Workup

  1. customthe phases were separated
  2. washThe combined organic phases were washed
  3. customdried
  4. customthe solvent was removed
  5. customThis gave 440 mg (86% of theory) of crude product (diastereomer ratio about 2:1) which was used for the next step without further purification

Sources & evidence

ORD record
ord-11f744b2f8304125bfb87c200cf6d58c
Source dataset
uspto-grants-2010_08
Patent number
US07786046B2

Reaction notes

Loading…