Diisopropyl diazene-1,2-dicarboxylate → HCID 71543646, compound

HRID 1746406Notes

Reaction equation

HRID 1746406 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=1)(=[O:12])=[O:11].[CH3:24][C:25]1[C:29]([CH2:30]O)=[C:28]([CH3:32])[O:27][N:26]=1.FC(F)(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)CCC1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>CN(C=O)C.O.CO.O.CN(C=O)C.O1CCCC1>[CH3:24][C:25]1[C:29]([CH2:30][O:19][C:15]2[CH:14]=[C:13]([S:10]([N:9]([C:3]3[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:1])[CH2:20][CH:21]([CH3:23])[CH3:22])(=[O:11])=[O:12])[CH:18]=[CH:17][CH:16]=2)=[C:28]([CH3:32])[O:27][N:26]=1

Participants

9

Reactant 4

HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2895753,5-Dimethyl-4-(hydroxymethyl)isoxazoleHCID 11422653[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Heptadecafluorodecyl)phenyl] diphenylphosphineHCID 86731581HCID 86731581, compound

Product 1

HCID 71543646HCID 71543646, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 21962138N,N-Dimethylformamide--water (1/1)SolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

N-(2,4-dimethylphenyl)-3-hydroxy-N-isobutylbenzenesulfonamide (76.9 mg, 0.231 mmol), (3,5-dimethylisoxazol-4-yl)methanol (36.7 mg, 0.288 mmol) and (4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl)diphenylphosphine (204 mg, 0.288 mmol) were added to a 2-5 mL Biotage microwave vessel. Tetrahydrofuran (THF) (4 mL) was added followed by diisopropyl diazene-1,2-dicarboxylate (DIAD) (0.056 mL, 0.288 mmol). The reaction vial was sealed and left to stir overnight at RT. The reaction mixture was concentrated in vacuo and then diluted with ethyl acetate (25 mL) and water (25 mL). The organic fraction was separated, dried and then concentrated in vacuo to give the crude product. The crude product was dissolved in DMF:H2O (9:1) 1 mL, and loaded onto a fluorous column (preconditioned with 1 mL DMF, followed by 6 mL MeOH:H2O (5:1). The semi purified fraction was eluted with 6 mL MeOH:H2O (5:1). The fraction was concentrated down, and dissolved in 1:1 MeOH:DMSO 1 mL and purified by mass directed autoPrep on Sunfire C18 column using Acetonitrile Water with a Formic acid modifier. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the required product, 37.7 mg.

Workup

  1. customThe reaction
  2. customvial was sealed
  3. waitleft
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. additiondiluted with ethyl acetate (25 mL) and water (25 mL)
  6. customThe organic fraction was separated
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customto give the crude product
  10. customThe semi purified fraction
  11. washwas eluted with 6 mL MeOH:H2O (5:1)
  12. concentrationThe fraction was concentrated down
  13. dissolutiondissolved in 1:1 MeOH
  14. customDMSO 1 mL and purified by mass
  15. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus

Sources & evidence

ORD record
ord-a23846dcea99404086248551a9934488
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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