Acetyl chloride → 3-(2-Amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid ethyl ester

HRID 1095421Notes

Reaction equation

HRID 1095421 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[S:7][C:8]([S:11][CH2:12][C:13]([CH3:18])([CH3:17])[C:14](O)=[O:15])=[CH:9][N:10]=1>C(O)C>[CH2:1]([O:3][C:14](=[O:15])[C:13]([CH3:17])([CH3:18])[CH2:12][S:11][C:8]1[S:7][C:6]([NH2:5])=[N:10][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 866378793-(2-Amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid

Product 1

HCID 574814293-(2-Amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetyl chloride (3.0 eq) was added drop wise to ethanol and stirred for additionally 30 min after completed addition. 3-(2-Amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid was added neat to this solution and the mixture was stirred at 50° C. for 18 h. The mixture was concentrated under reduced pressure and diluted with ethyl acetate and water. The strongly acidic solution was added NaHCO3 (aq; sat) to pH=8. The phases were separated and the aqueous phase extracted with additional ethyl acetate. The combined org. phases were washed with water and brine, dried (MgSO4), filtered and evaporated under reduced pressure to give 3-(2-amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid ethyl ester as brown crystals.

Workup

  1. additionaddition
  2. stirringthe mixture was stirred at 50° C. for 18 h
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additiondiluted with ethyl acetate and water
  5. additionThe strongly acidic solution was added NaHCO3 (aq; sat) to pH=8
  6. customThe phases were separated
  7. extractionthe aqueous phase extracted with additional ethyl acetate
  8. washphases were washed with water and brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c7ea7183acf24440bfb8c55b52fcb870
Source dataset
uspto-grants-2012_03
Patent number
US08138185B2

Reaction notes

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