Water → HCID 24780800, compound

HRID 2241815Notes

Reaction equation

HRID 2241815 reaction equation
[F:1][CH2:2][CH2:3][N:4]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][C:20]3[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:21]=3[N:22]=2)=[CH:14][N:13]=1)C(=O)OC(C)(C)C.FC(F)(F)C(O)=O.O.[OH-].[Na+]>C(Cl)Cl>[F:1][CH2:2][CH2:3][NH:4][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][C:20]3[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:21]=3[N:22]=2)=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59203840HCID 59203840, compound

Product 1

HCID 24780800HCID 24780800, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl (2-fluoroethyl)[5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-yl]carbamate (0.65 mmol) was dissolved in CH2Cl2 (20 mL), trifluoroacetic acid (0.5 mL) was added and the reaction mixture was stirred for 4 hours at r.t. Water (20 mL), NaOH (1.5 mL, 5M aq., pH adjusted to 12) and CH2Cl2 (20 mL) was added and the layers separated. The aqueous layer was extracted with CH2Cl2 (3×). The combined organic layers were dried (Na2SO4) filtered and concentrated. Purification using reverse phase HPLC afforded the title compound (78.0 mg). 1H NMR δ ppm 8.74 (d, 1H) 8.03 (dd, 1H) 7.60-7.64 (m, 1H) 7.58 (d, 1H) 7.35 (d, 1H) 6.95 (dd, 1H) 6.70 (d, 1H) 4.60-4.66 (m, 1H) 4.47-4.54 (m, 1H) 3.82 (s, 3H) 3.67-3.74 (m, 1H) 3.60-3.67 (m, 1H); ESI-MS m/z 288 (M+H).

Workup

  1. additionwas added
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification

Sources & evidence

ORD record
ord-e56380208400407f95bdca059ab566e5
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

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