Triphenylphosphine → HCID 68545252, compound

HRID 1445453Notes

Reaction equation

HRID 1445453 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[C:6](=[CH:11][CH:12]=1)[C:7]([O:9][CH3:10])=[O:8].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28]O)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].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>C1COCC1.C(OCC)C>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][O:13][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=2[C:7]([O:9][CH3:10])=[O:8])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 79523Methyl 4-methoxysalicylateHCID 735736Tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 68545252HCID 68545252, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-methoxysalicylate (7.91 g, 43.4 mmol), 2-(4-tert-butoxycarbonylpiperazin-1-yl)ethanol (10.0 g, 43.4 mmol), and triphenylphosphine (PPh3) (11.3 g, 43.4 mmol) in THF (190 ml) were cooled to 0° C. under N2. DIAD (8.54 ml, 43.4 mmol) was added dropwise, and the reaction allowed to warm to room temperature. After stirring for 18 h, the THF was removed in vacuo, the residue taken up in dichloromethane, and washed with water, dried, and the solvent removed in vacuo to give a yellow oil. After the oil was dissolved in diethyl ether and the solution allowed to stand for 18 h, the triphenylphosphine oxide was filtered, the solvent removed in vacuo, and the crude product purified on silica gel using preparative HPLC and a gradient of hexane and EtOAc to give 11.0 g (64.3%) of a pale yellow oil.

Workup

  1. customthe THF was removed in vacuo
  2. washwashed with water
  3. customdried
  4. customthe solvent removed in vacuo
  5. customto give a yellow oil
  6. waitto stand for 18 h
  7. filtrationthe triphenylphosphine oxide was filtered
  8. customthe solvent removed in vacuo
  9. customthe crude product purified on silica gel using preparative HPLC

Sources & evidence

ORD record
ord-e753c5a4e86e4b3e840354cab436202c
Source dataset
uspto-grants-2010_02
Patent number
US07666866B2

Reaction notes

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