Trifluoroacetic acid → HCID 59332857, compound

HRID 1880002Notes

Reaction equation

HRID 1880002 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][C:9]1([CH3:30])[CH2:15][O:14][C:13]2[CH:16]=[C:17](/[CH:20]=[CH:21]/[C:22]([O:24]C(C)(C)C)=[O:23])[CH:18]=[N:19][C:12]=2[NH:11][C:10]1=[O:29]>C(Cl)Cl>[CH3:8][C:9]1([CH3:30])[CH2:15][O:14][C:13]2[CH:16]=[C:17](/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23])[CH:18]=[N:19][C:12]=2[NH:11][C:10]1=[O:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57742070HCID 57742070, compound

Product 1

HCID 59332857HCID 59332857, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (3 mL) was added to a cooled solution of (E)-tert-butyl 3-(3,3-dimethyl-4-oxo-2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-8-yl)acrylate (1 g, 3 mmol) in CH2Cl2 (5 mL) and stirred for 30 min at rt. The mixture was evaporated and HCl/dioxane (4M, 5 mL) was added. The precipitate that formed was washed with ether and dried to afford the title compound (530 mg, 66%). 1H NMR (300 MHz, DMSO-d6) δ 8.45 (s, 1H), 8.28 (s, 1H), 7.82 (d, J=15.5 Hz, 1H), 6.84 (d, J=20 Hz, 1H), 4.05 (s, 2H), 1.47 (s, 6H).

Workup

  1. customThe mixture was evaporated
  2. additionHCl/dioxane (4M, 5 mL) was added
  3. customThe precipitate that formed
  4. washwas washed with ether
  5. customdried

Sources & evidence

ORD record
ord-b54faf99c4dc4138949ec893e5755cbd
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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