Sodium Chloride → HCID 18504018, compound

HRID 2269803Notes

Reaction equation

HRID 2269803 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5](OCOC)[C:4]=1[C:13]1[C:18]([CH:19]([OH:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:17][C:16]([CH2:27][S:28]([NH2:31])(=[O:30])=[O:29])=[CH:15][CH:14]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[Na+].[Cl-]>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:4]2[C:13]3[CH:14]=[CH:15][C:16]([CH2:27][S:28]([NH2:31])(=[O:30])=[O:29])=[CH:17][C:18]=3[CH:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[O:26][C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 18188546HCID 18188546, compound

Product 1

HCID 18504018HCID 18504018, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (4-(2-methoxy-6-methoxymethoxyphenyl)-5-(1-hydroxy-1-(2-pyridyl)methyl)phenyl methanesulfonamide (0.030 g, 0.075 mmol), prepared according to the procedures of Examples 32A-F, in THF (1 mL) was treated with tributylphoshine (0.045 g, 0.23 mmol) and 1,1′-(azodicarbonyl)dipiperidine (0.057 g, 0.23 mmol), stirred for 4 hours at room temperature, and treated with saturated NaCl (10 mL) and ethyl acetate (10 mL) to provide two layers. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The extract was dried (Na2SO4), filtered, and concentrated. The concentrate was purified by reverse phase HPLC with 20-100% CH3CN/water to provide the desired product. MS (ESI(−)Q1MS) m/z 381 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ9.83 (s, 1H), 8.53 (m, 1H), 8.31 (d, J=8 Hz, 1H), 7.79 (dt, J=8 Hz, 2 Hz, 1H), 7.39 (d, J=8 Hz, 1H), 7.32 (m, 1H), 7.22 (m, 1H), 7.18 (d, J=8 Hz, 1H), 6.93 (d, J=2 Hz, 1H), 6.75 (d, J=8 Hz, 1H), 6.70 (d, J=8 Hz, 1H), 6.21 (s, 1H), 3.90 (s, 3H), 3.00 (s, 3H).

Workup

  1. customto provide two layers
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe extract was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by reverse phase HPLC with 20-100% CH3CN/water

Sources & evidence

ORD record
ord-1c92f173ed614d4e87ea393813e61d0e
Source dataset
uspto-grants-2001_12
Patent number
US06329534B1

Reaction notes

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