1,4-Dioxane hydrochloride → HCID 86271762, compound

HRID 2277057Notes

Reaction equation

HRID 2277057 reaction equation
Cl.O1CCOCC1.[OH:8][C@@H:9]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][CH:28]2[CH2:32][CH2:31][CH2:30][O:29]2)[CH:21]=1)[CH2:10][CH2:11][NH:12]C(=O)OC(C)(C)C>C(Cl)Cl>[NH2:12][CH2:11][CH2:10][C@H:9]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][CH:28]2[CH2:32][CH2:31][CH2:30][O:29]2)[CH:21]=1)[OH:8]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 131733441HCID 131733441, compound

Product 1

HCID 86271762HCID 86271762, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HCl/dioxane (4M, 2.5 mL) was added at 0° C. to a solution of tert-butyl ((3R)-3-hydroxy-3-(3-((tetrahydrofuran-2-yl)methoxy)phenyl)propyl)carbamate (0.25 g, 0.71 mmol) in DCM (10 mL) and the reaction mixture was stirred at room temperature for 2 h. After completion of the reaction the solvent was removed under reduced pressure. Purification by column chromatography (MeOH:DCM with 1% aq. NH4OH, 1-10% gradient) gave Example 14 as a mixture of diastereomers as an off white semi-solid. Yield (0.22 g, 95%); 1H NMR (400 MHz, DMSO-d6): δ 7.20 (t, J=8.0 Hz, 1H), 6.87 (d, J=8.0 Hz, 2H), 6.78-6.76 (m, 1H), 4.64-4.61 (m, 1H), 4.15-4.11 (dd, 1H), 3.93-3.87 (m, 2H), 3.78-3.75 (m, 1H), 3.70-3.64 (m, 1H), 2.69-2.66 (m, 2H), 2.01-1.95 (m, 1H), 1.88-1.79 (m, 2H), 1.70-1.65 (dd, J=6.8 Hz, 3H); MS: m/z 252.14 [M+H]+.

Workup

  1. customAfter completion of the reaction the solvent
  2. customwas removed under reduced pressure
  3. customPurification by column chromatography (MeOH:DCM with 1% aq. NH4OH, 1-10% gradient)
  4. customgave Example 14
  5. additionas a mixture of diastereomers as an off white semi-solid
  6. customYield (0.22 g, 95%)

Sources & evidence

ORD record
ord-6863769b06374ea6babbead35725aa87
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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