Trifluoroacetic acid → HCID 86604636, compound

HRID 1593293Notes

Reaction equation

HRID 1593293 reaction equation
[O:1]=[C:2]1[N:8]([CH2:9][C:10]#[CH:11])[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[O:5][C@H:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@@H:3]1[NH:22]C(=O)OC(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:22][C@@H:3]1[C:2](=[O:1])[N:8]([CH2:9][C:10]#[CH:11])[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[O:5][C@@H:4]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86604637HCID 86604637, compound

Product 1

HCID 86604636HCID 86604636, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl [(2R,3S)-4-oxo-2-phenyl-5-prop-2-yn-1-yl-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]carbamate (67b) (125 mg, 0.318 mmol) was dissolved in 5:1 (v/v) dichloromethane:trifluoroacetic acid (4 mL) and kept at ambient temperature for 90 min. The solution was evaporated and the residue was dissolved in ethyl acetate and extracted with saturated aqueous sodium bicarbonate. The organic solution was dried and evaporated to afford the title compound (92 mg, 99%) as a white solid. 1H NMR (300 MHz, CDCl3) δ1.36 (br s, 2H), 2.29 (t, 1H, J=2.3 Hz), 4.10 (m, 1H), 4.56 and 4.61 (dd, 1H, J=2.4 Hz), 4.76 and 4.81 (dd, 1H, J=2.4 Hz), 5.46 (d, 1H, J=7.4 Hz), 7.27 (m, 3H), 7.38 (m, 3H), 7.47 (m, 3H). MS APCI, m/z=293 (M+1). LC/MS: 1.63 min.

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. extractionextracted with saturated aqueous sodium bicarbonate
  4. customThe organic solution was dried
  5. customevaporated

Sources & evidence

ORD record
ord-71fab12eb18c47d393147b3ccfe043c4
Source dataset
uspto-grants-2007_11
Patent number
US07294622B2

Reaction notes

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