1,4-Dioxane hydrochloride → HCID 86271673, compound

HRID 2277054Notes

Reaction equation

HRID 2277054 reaction equation
Cl.O1CCOCC1.[OH:8][C@@H:9]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=2)[CH:21]=1)[CH2:10][CH2:11][NH:12]C(=O)OC(C)(C)C>CO>[NH2:12][CH2:11][CH2:10][C@H:9]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=2)[CH:21]=1)[OH:8]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 131733439HCID 131733439, compound

Product 1

HCID 86271673HCID 86271673, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

HCl/dioxane (4M, 2 mL) was added at 0° C. to a solution of (R)-tert-butyl (3-hydroxy-3-(3-((6-methylpyridin-2-yl)methoxy)phenyl)propyl)carbamate (200 mg, 0.54 mmol) in MeOH (3 mL) and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure to give after purification by triturating in diethyl ether Example 12 hydrochloride as a white solid. Yield (0.15 g, 52%); 1H NMR (400 MHz, DMSO-d6) δ 7.92 (bs, 1H), 7.74 (bs, 3H), 7.47 (bs, 1H), 7.40 (bs, 1H), 7.28 (t, J=8.0 Hz, 1H), 7.02 (s, 1H), 6.95-6.90 (m, 2H), 5.20 (s, 2H), 4.68-4.65 (m, 1H), 2.84 (bs, 2H), 2.56 (s, 3H), 1.88-1.83 (m, 2H); MS: m/z 273.20 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give
  3. customafter purification
  4. customby triturating in diethyl ether Example 12 hydrochloride as a white solid
  5. customYield (0.15 g, 52%)

Sources & evidence

ORD record
ord-063cd72bb75d4a33863ee0e3be4a473b
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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