Ethyl Acetate → HCID 56949611, compound

HRID 1518930Notes

Reaction equation

HRID 1518930 reaction equation
[CH2:1]([O:8][C:9]1[C:23]([N+:24]([O-])=O)=[CH:22][C:21]([F:27])=[C:20]([CH3:28])[C:10]=1[C:11]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+].CCOC(C)=O>C1COCC1.O>[NH2:24][C:23]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([C:20]([CH3:28])=[C:21]([F:27])[CH:22]=1)[C:11]([O:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24489Sodium DithioniteHCID 58493293HCID 58493293, compound

Product 1

HCID 56949611HCID 56949611, compoundYield 108.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 65 (700 g, 1.84 mol) in THF (7 L) was cooled to 12° C. and stirred while adding a solution of Na2S2O4 (1599 g, 9.18 mol) in water (7.0 L) was added to the reaction with stirring. The exotherm was controlled by addition rate so that the reaction mixture temperature was below 17° C. The reaction mixture was then allowed to stir for 15 hours prior to adding 15.3 L EtOAc. The layers were separated and the organic layer was washed with successively with water (2×4 L and brine (1×4 L). The organic was dried over Na2SO4 and concentrated to give 699 g of a brownish solid that was recrystallized from heptane/toluene to afford 532 g (82.7%) of desired compound 66 obtained as an off-white solid.

Workup

  1. additionwas added to the reaction
  2. stirringwith stirring
  3. additionThe exotherm was controlled by addition rate so that the reaction mixture temperature
  4. customwas below 17° C
  5. stirringto stir for 15 hours
  6. customThe layers were separated
  7. washthe organic layer was washed with successively with water (2×4 L and brine (1×4 L)
  8. dry with materialThe organic was dried over Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-eae846c0899d4cd992a46968f8e0eea6
Source dataset
uspto-grants-2015_07
Patent number
US09073829B2

Reaction notes

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