Methanol → HCID 131723896, compound

HRID 413351Notes

Reaction equation

HRID 413351 reaction equation
Cl.[NH2:2][C@@:3]([C:7]([OH:9])=[O:8])([CH3:6])[CH2:4][CH3:5].[Cl-].[Na+].S(Cl)([Cl:14])=O.[CH3:16][OH:17]>>[CH3:5][CH:4]([CH3:16])[C@@:3]([NH2:2])([CH3:6])[C:7]([OH:9])=[O:8].[ClH:14].[CH3:16][O:17][C:7](=[O:8])[C@:3]([CH3:6])([CH2:4][CH3:5])[NH2:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 5234Sodium ChlorideHCID 24386Thionyl ChlorideHCID 12304636HCID 12304636, compound

Product 1

HCID 131723896HCID 131723896, compound

Procedure

To a well-stirred suspension of the previous mixture of (S)-isovaline hydrochloride and sodium chloride in methanol (3 L) was slowly added thionyl chloride (373 g, 3.13 mole). After the addition was complete the reaction mixture was refluxed for 3 hours. The resulting mixture was cooled to room temperature and filtered. The resulting white filter cake was washed several times with methanol. The combined methanol filtrate and washings were concentrated using a rotary evaporator. Toluene was added to the resulting crude residue and then removed using the rotary evaporator yielding 187 g of the expected (S)-isovaline methyl ester hydrochloride.

Workup

  1. additionAfter the addition
  2. temperaturewas refluxed for 3 hours
  3. filtrationfiltered
  4. washThe resulting white filter cake was washed several times with methanol
  5. concentrationThe combined methanol filtrate and washings were concentrated
  6. customa rotary evaporator
  7. additionToluene was added to the resulting crude residue
  8. customremoved
  9. customthe rotary evaporator

Sources & evidence

ORD record
ord-f0c9512e2c034be5a6b7dbae651be5b1
Source dataset
uspto-grants-2003_05
Patent number
US06566403B1

Reaction notes

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