Triphenylphosphine → HCID 44218291, compound

HRID 1958833Notes

Reaction equation

HRID 1958833 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH2:21][N:22]([CH2:24][CH3:25])[CH3:23])[CH:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:26])[C:4]=1[OH:27])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC1(C)[O:52][C@H:51]([CH2:53]O)[CH2:50][O:49]1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH2:21][N:22]([CH2:24][CH3:25])[CH3:23])[CH:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:26])[C:4]=1[O:27][CH2:53][C@@H:51]([OH:52])[CH2:50][OH:49])[CH3:2]

Participants

7

Reactant 4

HCID 11776Triphenylphosphine2×HCID 736056(R)-Solketal2×HCID 5462977Diethyl azodicarboxylateHCID 136331245HCID 136331245, compound

Product 1

HCID 44218291HCID 44218291, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-ethyl-4-(5-{3-[(ethyl-methyl-amino)-methyl]-5-methyl-phenyl}-[1,2,4]oxadiazol-3-yl)-6-methyl-phenol (99 mg, 271 μmol) in THF (2 mL), PPh3 (107 mg, 406 μmol) and (R)-2,2-dimethyl-1,3-dioxolane-4-methanol (36 mg, 271 μmol) were added. The mixture was cooled to 0° C. and DEAD (177 mg, 406 μmol, 186 μL of a 40% solution in toluene) was added. Stirring was continued at 0° C. for 10 min, then at rt for 1 h before another portion of PPh3 (107 mg, 406 μmol) and (R)-2,2-dimethyl-1,3-dioxolane-4-methanol (36 mg, 271 μmol) was added. Stirring was continued for 1 h and the reaction mixture was separated by prep. HPLC. The product containing fraction were combined, evaporated and dissolved in MeCN (1.5 mL) and 1N aq. HCl (0.4 mL). The mixture was stirred at rt for 10 min before it was again separated by prep. HPLC to give the title compound as a colourless resin (27 mg). LC-MS**: tR=0.56 min; [M+1]+=440.21; 1H NMR (D6-DMSO): δ 1.06 (t, J=7.0 Hz, 3H), 1.23 (t, J=7.0 Hz, 3H), 2.15 (s, 3H), 2.36 (s, 3H), 2.42-2.47 (m, 5H), 2.75 (q, J=7.3 Hz, 2H), 3.50 (d, J=4.8 Hz, 2H), 3.56 (s, 2H), 3.72-3.78 (m, 1H), 3.83-3.89 (m, 2H), 7.47 (s, 1H), 7.79 (s, 2H), 7.91 (s, 1H), 8.18 (s, 1H).

Workup

  1. stirringStirring
  2. waitwas continued for 1 h
  3. customthe reaction mixture was separated by prep
  4. additionThe product containing fraction
  5. customevaporated
  6. dissolutiondissolved in MeCN (1.5 mL)
  7. stirringThe mixture was stirred at rt for 10 min before it
  8. customwas again separated by prep

Sources & evidence

ORD record
ord-a08e74429ebd4b318706571750fd9440
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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