Pyridine → HCID 90060285, compound

HRID 1779250Notes

Reaction equation

HRID 1779250 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:14][OH:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[C:24](OC(=O)C)(=[O:26])[CH3:25].N1C=CC=CC=1>ClCCl.[Cl-].[Na+].O>[C:24]([O:15][CH2:14][C@@H:13]([NH:16][C:17]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:23])[CH2:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:7][CH:8]=1)(=[O:26])[CH3:25]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 118182222HCID 118182222, compound

Product 1

HCID 90060285HCID 90060285, compoundYield 102.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

tert-Butyl [(S)-2-(4-but-2-ynyloxy-phenyl)-1-hydroxymethyl-ethyl]-carbamate (402 mg, 1.26 mmol) was dissolved in dichloromethane (6.3 mL), and acetic anhydride (0.179 mL, 1.89 mmol) and pyridine (204 μL, 2.52 mmol) were added at room temperature. The reaction mixture was stirred for 7 hours, then poured into a saturated brine, and extracted with ethyl acetate. The organic extract was dried over magnesium sulfate, and concentrated under reduced pressure to obtain the title compound (468 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aa34eed91c274ba79a992e5031151320
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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