Hydrochloric Acid → HCID 58997956, compound

HRID 2267623Notes

Reaction equation

HRID 2267623 reaction equation
[N:1]([C@@H:4]1[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[O:6][C@@H:5]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[N+]=[N-].Cl>C(O)C.[Pd]>[NH2:1][C@@H:4]1[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[O:6][C@@H:5]1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59688509HCID 59688509, compound

Product 1

HCID 58997956HCID 58997956, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2R,3S)-3-azido-2-phenyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one (64d) (1.128 g, 4.024 mmol)) in ethanol (80 mL) was added 1N hydrochloric acid (4.43 mL) and 5% palladium on carbon (60 mg). The reaction was purged with hydrogen and stirred for 2 h under a balloon of hydrogen. The reaction was purged with nitrogen then filtered through diatomaceous earth. The solvent was evaporated to afford a white solid that was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate while stirring. The organic phase was separated and the aqueous phase extracted an additional two times with ethyl acetate. The combined organic extracts were dried, filtered and evaporated to afford the title compound (973 mg, 95%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ1.36 (br, 2H), 3.93 (d, 1H, J=6.2 Hz), 5.45 (d, 1H, J=6.2 Hz), 7.06-7.22 (m, 4H), 7.32-7.46 (m, 5H), 9.96 (br, 1H). MS APCI, m/z=255 (M+1). LC/MS: 1.29 min.

Workup

  1. customThe reaction was purged with hydrogen
  2. customThe reaction was purged with nitrogen
  3. filtrationthen filtered through diatomaceous earth
  4. customThe solvent was evaporated
  5. customto afford a white solid
  6. customthat was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  7. stirringwhile stirring
  8. customThe organic phase was separated
  9. extractionthe aqueous phase extracted an additional two times with ethyl acetate
  10. customThe combined organic extracts were dried
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-3626ba342a3a4747b118338c1cf1d84a
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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