Pyridine → HCID 58787677, compound

HRID 1375727Notes

Reaction equation

HRID 1375727 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([C@@:8]2([F:25])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[N:10]([C:21](Cl)=[O:22])[C:9]2=[O:24])[CH:7]=1.N1C=CC=CC=1.[C:34]([O:38]CC1C=CC=CC=1)(=[O:37])[CH2:35][OH:36]>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([C@@:8]2([F:25])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=3)[N:10]([C:21]([O:36][CH2:35][C:34]([OH:38])=[O:37])=[O:22])[C:9]2=[O:24])[CH:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 561337Benzyl 2-hydroxyacetateHCID 58787639HCID 58787639, compound

Product 1

HCID 58787677HCID 58787677, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-XI in toluene and methylene chloride was added 0.6 mL of pyridine followed by the addition of benzyl glycolate (0.878 mL). The resulting mixture was stirred at room temperature for an hour. This reaction mixture was diluted with dichloromethane and washed with water. The organic layer was dried over Na2SO4 and condensed by rotary evaporation. The residue was chromatographed on a silica gel flash column packed with ethyl acetate: hexane (v/v, 10:1) and washed with dichloromethane to afford 1.32 g of the title compound.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over Na2SO4 and condensed by rotary evaporation
  3. customThe residue was chromatographed on a silica gel flash column
  4. washhexane (v/v, 10:1) and washed with dichloromethane

Sources & evidence

ORD record
ord-6b9a6198e3454fcb80c4f52f578aefc4
Source dataset
uspto-grants-2007_01
Patent number
US07169803B2

Reaction notes

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