2,4,6-Trimethylpyridine → HCID 131719871, compound

HRID 1598421Notes

Reaction equation

HRID 1598421 reaction equation
[Si:1]([O:8][C:9]1([O:16][C@@H:15]([CH3:17])[C@@H:13]([OH:14])[C@@H:12]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:11]1)[OH:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C(C)=CC(C)=CC=1C.[Br:34][CH2:35][C:36](Br)=[O:37].ClCl>C(Cl)Cl.O>[Si:1]([O:8][C:9]1([O:16][C@@H:15]([CH3:17])[C@@H:13]([O:14][C:36](=[O:37])[CH2:35][Br:34])[C@@H:12]([NH:18][C:19](=[O:24])[C:20]([F:22])([F:21])[F:23])[CH2:11]1)[OH:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 24526ChlorineHCID 61147Bromoacetyl bromideHCID 131719872HCID 131719872, compound

Product 1

HCID 131719871HCID 131719871, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-t-butyl dimethylsilyloxy-3-trifluoroacetamido-2,3,6-trideoxy-L-lyxohexopyranose (81 mg, 0.18 mmol) in CH2Cl2 (2 ml) at 0° C. were added collidine (47 μl, 0.36 mmol), and bromoacetylbromide (24 μl, 0.27 mmol). After 1 hour, the reaction mixture was worked up with CH2 Cl2 and water. The organic layer was washed with brine and dried over MgSO4. The solvent was evaporated to give the titled compound (76 mg, 74%).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9f7e0666668b4008aa2bb021d9ed4d92
Source dataset
uspto-grants-1998_04
Patent number
US05736523

Reaction notes

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