Citric Acid → HCID 69627370, compound

HRID 1582906Notes

Reaction equation

HRID 1582906 reaction equation
[C:1]([C:8]1[N:9]=[C:10]([C:15](=O)[NH2:16])[S:11][C:12]=1[CH2:13][NH2:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(C(C)C)CC)(C)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl.O>[C:1]([C:8]1[N:9]=[C:10]([C:15]#[N:16])[S:11][C:12]=1[CH2:13][NH2:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 9845Trifluoroacetic anhydrideHCID 81531DiisopropylethylamineHCID 69627164HCID 69627164, compound

Product 1

HCID 69627370HCID 69627370, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4.95 g (19.24 mmol) of 4-Boc-aminomethyl-2-carbamoylthiazole were introduced into 90 ml of methylene chloride and 16.7 ml (97.44 mmol) of diisopropylethylamine, the mixture was cooled to 0° C., a solution of 6.35 ml of trifluoroacetic anhydride in 10 ml of methylene chloride was added dropwise at 0 to 5° C., and the mixture was subsequently warmed to room temperature (TLC check). Then, 25 ml of water were added, the mixture was stirred for 30 minutes at room temperature and brought to pH 2.5 with 10% strength citric acid solution, and the organic phase was washed repeatedly, dried using magnesium sulfate and concentrated in vacuo. 5.4 g of viscous, pale brown crude product resulted, which were employed in the next step without further purification.

Workup

  1. temperaturethe mixture was subsequently warmed to room temperature (TLC check)
  2. washthe organic phase was washed repeatedly
  3. customdried
  4. concentrationconcentrated in vacuo
  5. custom5.4 g of viscous, pale brown crude product resulted
  6. customwhich were employed in the next step without further purification

Sources & evidence

ORD record
ord-379fc61a7aa4446a8c8181a1904ec94e
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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