Trifluoroacetic acid → HCID 67272110, compound

HRID 601703Notes

Reaction equation

HRID 601703 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([F:32])[CH:31]=1)[CH2:5][C@H:6]1[C@@H:10]([C@H:11]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][N:12]2C(OC(C)(C)C)=O)[O:9][C:8](=[O:28])[NH:7]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([F:32])[CH:31]=1)[CH2:5][C@H:6]1[C@@H:10]([C@H:11]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][NH:12]2)[O:9][C:8](=[O:28])[NH:7]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57881037HCID 57881037, compound

Product 1

HCID 67272110HCID 67272110, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-tert-butyl 3-((4S,5S)-4-(3,5-difluorobenzyl)-2-oxooxazolidin-5-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (Step A (6), 400 mg) in CH2Cl2 (20 mL) was treated with TFA (10 mL). This reaction mixture was stirred at rt for 3 h. The mixture was then concentrated in vacuo with addition of toluene. The residue was partitioned between ethyl acetate (200 mL) and aqueous sodium carbonate solution. The organic phase was washed again with aqueous sodium carbonate solution, H2O, and dried (Na2SO4), and concentrated in vacuo to give 320 mg (100% yield) of the title compound: 1H NMR (CDCl3, 500 MHz) δ 2.62 (1H, dd, J=10, 15 Hz), 2.66 (1H, dd, J=10, 15 Hz), 3.10 (1H, dd, J=5, 15 Hz), 3.24 (1H, dt, J=5, 10 Hz), 3.33 (1H, dd, J=5, Hz), 3.98 (2H, s), 4.05 (1H, m), 4.39 (1H, m), 5.64 (1H, s), 6.70 (1H, m), 6.76 (2H, d, J=10 Hz), 7.02 (1H, t, J=5 Hz), 7.12-7.17 (3H, m).

Workup

  1. concentrationThe mixture was then concentrated in vacuo with addition of toluene
  2. customThe residue was partitioned between ethyl acetate (200 mL) and aqueous sodium carbonate solution
  3. washThe organic phase was washed again with aqueous sodium carbonate solution, H2O
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6120d7de78f742d2ae84b749edea2a25
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Reaction notes

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