Sulfuric Acid → 3-Methyl-2-(phenylformamido)butanoic acid

HRID 1382919Notes

Reaction equation

HRID 1382919 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][CH:11]([C:15]([OH:17])=[O:16])[CH:12]([CH3:14])[CH3:13].[OH-].[Na+].S(=O)(=O)(O)O>O1CCCC1>[C:1]([NH:10][CH:11]([C:15]([OH:17])=[O:16])[CH:12]([CH3:14])[CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 1182DL-valineHCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 2266823-Methyl-2-(phenylformamido)butanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.1 kg. (36.28 moles) of benzoyl chloride is added portionwise to a mixture of 3.5 kg. (29.88 moles) of DL-valine, 39.0 1. of 2N. sodium hydroxide solution (78 moles) and 7 1. of tetrahydrofuran stirred at ~10° C. at a rate such that the temperature is maintained at 10° -15° C., and the reaction mixture is warmed to ~20° C. and stirred at ~20° C. for 3 hours, the reaction mixture being stirred under nitrogen throughout. 1.4 1. of concentrated sulfuric acid is carefully added at a rate such that the temperature does not exceed 25° C., and the mixture is cooled to ~5°-10° C. and stirred at this temperature for about 30 minutes to obtain a solid. (If necessary, the mixture is seeded.) The resulting solid is collected by filtration, washed three times with 20 1. portions of hot water, washed three times with 20 1. portions of hexane and dried at 40° C. and reduced pressure for ~12 hours to obtain the product (6.4 kg.), m.p. 123°-126° C.

Workup

  1. temperatureis maintained at 10° -15° C.
  2. temperaturethe reaction mixture is warmed to ~20° C.
  3. stirringthe reaction mixture being stirred under nitrogen throughout
  4. customdoes not exceed 25° C.
  5. temperaturethe mixture is cooled to ~5°-10° C.
  6. stirringstirred at this temperature for about 30 minutes
  7. customto obtain a solid
  8. filtration) The resulting solid is collected by filtration
  9. washwashed three times with 20 1
  10. washportions of hot water, washed three times with 20 1
  11. dry with materialportions of hexane and dried at 40° C.
  12. customreduced pressure for ~12 hours to obtain the product (6.4 kg.), m.p. 123°-126° C.

Sources & evidence

ORD record
ord-d7e66f3c7fee44fbb2625973df5027a7
Source dataset
uspto-grants-1989_02
Patent number
US04808607

Reaction notes

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