HCID 67363725, compound → 76687-08-6

HRID 524404Notes

Reaction equation

HRID 524404 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C:5]([C:8]1[N:9]=[C:10]([N:13](C(OC(C)(C)C)=O)CC2C=CC(OC)=CC=2)[S:11][CH:12]=1)([CH3:7])[CH3:6])[CH3:2]>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4](=[O:30])[C:5]([C:8]1[N:9]=[C:10]([NH2:13])[S:11][CH:12]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

3

Reactant 1

HCID 67363725HCID 67363725, compound

Product 1

HCID 8366865176687-08-6Yield 94.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-{2-[tert-Butoxycarbonyl-(4-methoxy-benzyl)-amino]-thiazol-4-yl}-2-methyl-propionic acid ethyl ester (1.5 g, 3.45 mmol) was refluxed in 15 mL of trifluoroacetic acid for 18 hrs. Trifluoroacetic acid was removed in vacuo and the residue was partitioned between water (50 mL) and ethyl acetate (50 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with brine and dried over anhydrous sodium sulphate and the solvent was removed in vacuo to get the solid product (0.7 g).

Workup

  1. customTrifluoroacetic acid was removed in vacuo
  2. customthe residue was partitioned between water (50 mL) and ethyl acetate (50 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-23799c0d042841aa848bb3c4d2df0377
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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