HCID 68461424, compound → HCID 21015128, compound

HRID 507431Notes

Reaction equation

HRID 507431 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][S:8][CH:7]([CH2:10][CH:11]([C:20]([O:22]CC2C=CC=CC=2)=O)[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[NH:6]1)=[O:4]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][S:8][CH:7]2[CH2:10][CH:11]([NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[C:20](=[O:22])[N:6]12)=[O:4]

Participants

4

Reactant 1

HCID 68461424HCID 68461424, compound

Product 1

HCID 21015128HCID 21015128, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 3 (1.4 g, 3.3 mmol) in 20 mL of pyridine was added 0.1 g DMAP and the mixture was refluxed overnight. After removal of the pyridine, the residue was partitioned between water and ethyl acetate. The organic phase was dried, concentrated and purified by column chromatography on silica gel to afford the pure product (0.5 g, 48%) 1H NMR (400 MHz, CDCl3) δ1.44 (s, 9 H), 2.01 (m, 1 H), 3.19 (m, 1H), 3.77 (d, 3 H), 4.12 (m, 1 H), 5.08-5.16 (m, 3 H).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customAfter removal of the pyridine
  3. customthe residue was partitioned between water and ethyl acetate
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6d835acd58324403a947fe9817c0ca61
Source dataset
uspto-grants-2010_08
Patent number
US07786163B2

Reaction notes

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