HCID 11394853, compound → HCID 86601464, compound

HRID 1170792Notes

Reaction equation

HRID 1170792 reaction equation
[C:1]([O:4][CH2:5][C:6]([NH:20]C(=O)OC(C)(C)C)([CH2:15][O:16][C:17](=[O:19])[CH3:18])[C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:3])[CH3:2].[ClH:28].O1CCOCC1>>[Cl-:28].[C:1]([O:4][CH2:5][C:6]([CH2:15][O:16][C:17](=[O:19])[CH3:18])([NH3+:20])[C:7](=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 11394853HCID 11394853, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 86601464HCID 86601464, compoundYield 53%

Procedure

tert-butyl 3-acetoxy-2-(acetoxymethyl)-1-oxo-1-phenylpropan-2-ylcarbamate (2) (420 mg, 1.1 mmol, 1.0 equiv.) was added to a 100 mL RBF and a 4.0 N HCl-Dioxane solution (8.3 mL, 33.0 mmol, 30.0 equiv) was added. The solution was stirred for 25 min and the solvent was evaporated with a steady stream of N2 (g). The resulting residue was taken up in Et2O (40 mL) giving a sticky solid. The mixture was cooled by partial evaporation and the solid was triturated and stirred for 10 min. The precipitate was filtered, washed with Et2O (2×50 mL), and dried under vacuum to give 180 mg (53%) of 4 as a white solid. mp=122-123° C.; 1H NMR (500 MHz, DMSO) δ 9.01 (br s, 3H, C—NH3), 7.97 (d, J=7.0 Hz, 2H, Ph-H), 7.72 (t, J=7.5 Hz, 1H, Ph-H), 7.58 (t, J=7.5 Hz, 2H, Ph-H), 4.78 (AB, J=12.5 Hz, 2H, CCH2), 4.66 (AB, J=12.5 Hz, 2H, C—CH2), 1.97 (s, 6H, (O═C—CH3)2); 13C NMR (125 MHz, DMSO) δ 193.8, 169.4, 133.7, 133.6, 129.0, 128.2, 67.2, 62.8, 20.4; LRMS (ESI-MS m/z): Mass calcd for C14H18NO5 [M]+, 280.30. Found 280.

Workup

  1. customthe solvent was evaporated with a steady stream of N2 (g)
  2. customgiving a sticky solid
  3. temperatureThe mixture was cooled by partial evaporation
  4. customthe solid was triturated
  5. stirringstirred for 10 min
  6. filtrationThe precipitate was filtered
  7. washwashed with Et2O (2×50 mL)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-3f0d8d2e55b342b0adbcb4c6e6be3347
Source dataset
uspto-grants-2010_11
Patent number
US07829304B2

Reaction notes

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