Trifluoroacetic acid → HCID 86604636, compound

HRID 2267630Notes

Reaction equation

HRID 2267630 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-27c6b77542974914a0fae42c11ef92e6
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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