Triphenylphosphine → HCID 67172143, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[NH:16][N:15]=[CH:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].O[CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.CCO.Cl>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH:13]=[CH:14][N:15]([CH2:18][CH2:19][NH2:20])[N:16]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
5-(3-methoxy-4-nitrophenyl)-1H-pyrazole (0.555 g, 2.53 mmol), tert-butyl 2-hydroxyethylcarbamate (0.449 g, 2.79 mmol) and triphenylphosphine (0.863 g, 3.29 mmol) and THF (20 ml) were mixed. DIAD (0.997 ml, 5.06 mmol) was added. The mixture was stirred for 3 h. 10% EtOH/HCl (50 ml) was added. The mixture was stirred overnight. The solvent was removed by evaporation. Water (20 ml) was added to the residue. This mixture was washed with DCM (2×20 ml). 1 M NaOH was added until pH 14 was reached followed by extraction with DCM (3×20 ml). The organic layers were pooled and evaporated to dryness. Flash chromatography (gradient of DCM:MeOH) gave 97 mg of the title compound. 1H-NMR (400 MHz; CDCl3): δ 3.19-3.26 (m, 2H), 4.04 (s, 3H), 4.20-4.28 (m, 2H), 6.63 (m, 1H), 7.38-7.43 (m, 1H), 7.52 (m. 1H), 7.59 (m, 1H), 7.91-7.97 (m, 1H).
Workup
- stirringThe mixture was stirred overnight
- customThe solvent was removed by evaporation
- additionWater (20 ml) was added to the residue
- washThis mixture was washed with DCM (2×20 ml)
- addition1 M NaOH was added until pH 14
- extractionwas reached followed by extraction with DCM (3×20 ml)
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-26bcc70240c541599e9133466b1c7864
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975254B2
Reaction notes
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