N,N,N',N'-Tetramethylazodicarboxamide → HCID 68537736, compound

HRID 2389326Notes

Reaction equation

HRID 2389326 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:17])[N:12]([CH2:14][CH2:15][OH:16])[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N(C(N(C)C)=O)=NC(N(C)C)=O.C(P(CCCC)CCCC)CCC.O[C:50]1[CH:51]=[C:52]([S:56][CH2:57][CH2:58][CH2:59][C:60]([O:62][CH2:63][CH3:64])=[O:61])[CH:53]=[CH:54][CH:55]=1>C1(C)C=CC=CC=1.CCOC(C)=O>[C:18]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:17])[N:12]([CH2:14][CH2:15][O:16][C:54]3[CH:53]=[C:52]([S:56][CH2:57][CH2:58][CH2:59][C:60]([O:62][CH2:63][CH3:64])=[O:61])[CH:51]=[CH:50][CH:55]=3)[CH:13]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 68535543HCID 68535543, compoundHCID 68536260HCID 68536260, compound

Product 1

HCID 68537736HCID 68537736, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(diphenylmethyl)-1-(2-hydroxyethyl)pyridin-2(1H)-one (300 mg) in toluene (4.0 mL) were added 1,1′-azobis(N,N-dimethylformamide) (203 mg) and tributylphosphine (291 μL) at ambient temperature. And then to the mixture was added a solution of ethyl 4-[(3-hydroxyphenyl)sulfanyl]butanoate (378 mg) in toluene (2.0 mL) at 0° C. After stirring at ambient temperature for an hour, the reaction mixture was diluted with EtOAc (10 mL). The mixture was washed with water (10 mL) and brine (10 mL). The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo to give crude oil. The oil was purified by silica gel column chromatography(n-hexane:EtOAc=4:1-1:1) to give ethyl 4-[(3-{2-[5-(diphenylmethyl)-2-oxopyridin-1(2H)-yl]ethoxy}phenyl)sulfanyl]butanoate (436 mg) as a colorless oil.

Workup

  1. washThe mixture was washed with water (10 mL) and brine (10 mL)
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto give crude oil
  6. customThe oil was purified by silica gel column chromatography(n-hexane:EtOAc=4:1-1:1)

Sources & evidence

ORD record
ord-79430ca9195f4c6aa3ed22b9257188d5
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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