Triphenylphosphine → HCID 178498280, compound

HRID 1787936Notes

Reaction equation

HRID 1787936 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([OH:15])[CH:6]=1.[C:16]([O:20][C:21]([NH:23][C@H:24]1[CH2:29][CH2:28][C@H:27](O)[CH2:26][CH2:25]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCCCCC.C(OCC)(=O)C>[C:16]([O:20][C:21]([NH:23][C@@H:24]1[CH2:29][CH2:28][C@H:27]([O:15][C:7]2[CH:6]=[C:5]([O:4][CH2:3][CH2:2][F:1])[CH:14]=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])[CH2:26][CH2:25]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10420774Methyl 4-(2-Fluoroethoxy)-2-hydroxybenzoateHCID 178418329HCID 178418329, compound

Product 1

HCID 178498280HCID 178498280, compoundYield 71.7%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Using a procedure similar to that of Example 6-D, methyl 4-(2-fluoroethoxy)-2-hydroxybenzoate (5.0 g, 24.75 mmol), trans-4-tert-butoxycarbonylaminocyclohexanol (5.02 g, 24.75 mmol), and triphenylphosphine (1.2 equivalents) in THF (125 mL) is treated with diethyl azodicarboxylate (1.3 equivalents) in THF (25 mL). After having stirred overnight at room temperature, the reaction mixture was heated 8 h at 40-50° C., then stirred overnight at room temperature. The crude product was isolated by elution from silica gel with a gradient of 0 to 40% ethyl acetate in hexane to afford crude methyl 2-(cis-4-tert-butoxycarbonylaminocyclohexyloxy)-4-(2-fluoroethoxy)benzoate (7.30 g), which is used without further purification.

Workup

  1. temperaturethe reaction mixture was heated 8 h at 40-50° C.
  2. stirringstirred overnight at room temperature

Sources & evidence

ORD record
ord-0fe4a2024130415982a1cf7bb40535a2
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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