Ethyl Acetate → HCID 12016496, compound

HRID 1264616Notes

Reaction equation

HRID 1264616 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:28]([O-])=O)=[C:6]([CH:27]=1)[CH2:7][N:8]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:9]([CH2:14][OH:15])[C:10]([O:12][CH3:13])=[O:11].O.O.[Sn](Cl)(Cl)(Cl)Cl.[C:38]([O-])(O)=O.[Na+].C(O[CH2:47][CH3:48])(=O)C>C(O)C>[NH2:28][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:27][C:6]=1[CH2:7][N:8]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:38]#[C:47][CH3:48])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:9]([CH2:14][OH:15])[C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 18612902HCID 18612902, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 12016496HCID 12016496, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 2-{(5-fluoro-2-nitrobenzyl)[(4-methoxyphenyl)sulfonyl]amino}-3-hydroxypropanoate (1.0 g, 2.08 mmol) was dissolved in ethanol (18 mL). To this was added tin chloride dihydrate (2.35 g, 10.4 mmol) and the reaction was heated to 70° C. for 2 hours. The reaction was then cooled to room temperature and ice water followed by NaHCO3 was added to bring the solution to pH 8. Ethyl acetate was added and the suspension was filtered through celite. The organic layer was separated and washed with brine, dried over Na2SO4 concentrated in vacuo and chromatographed using 1:1 hexane:ethyl acetate as eluant to provide 0.55 g (58%) of the desired product as a yellow oil.

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. additionwas added
  3. filtrationthe suspension was filtered through celite
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customchromatographed

Sources & evidence

ORD record
ord-c775419fbf1d4407a48e9b8f18c7a213
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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