Triphenylphosphine → Rac-[1-(4-chloro-phenyl)-2-oxo-2-[4-(tetrahydro-pyran-3-yloxy)-phenyl]-ethyl]-carbamic acid tert-butyl ester

HRID 384906Notes

Reaction equation

HRID 384906 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:45]1[CH2:50][CH2:49][CH2:48][CH:47](O)[CH2:46]1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>O1CCCC1>[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]([C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)[C:9](=[O:10])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:47]2[CH2:48][CH2:49][CH2:50][O:45][CH2:46]2)=[CH:13][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 12256033tetrahydro-2H-pyran-3-olHCID 68409176Rac-[1-(4-chloro-phenyl)-2-(4-hydroxy-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 68408312Rac-[1-(4-chloro-phenyl)-2-oxo-2-[4-(tetrahydro-pyran-3-yloxy)-phenyl]-ethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 250 mg (0.691 mmol) rac-[1-(4-chloro-phenyl)-2-(4-hydroxy-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester, 257 mg (0.864 mmol) triphenylphosphine and 84.7 mg (0.829 mmol) tetrahydro-pyran-3-ol in 8.5 ml tetrahydrofuran were added 191 mg (0.829 mmol) di-tert-butyl azodicarboxylate and the reaction mixture stirred at ambient temperature for 2 hours. Then the reaction mixture was evaporated and purified by flash chromatography on silica gel with a heptane/ethyl acetate gradient of 0-30% ethyl acetate. The title compound was obtained as colorless solid: MS (ISN): 444.2 (M−H)−.

Workup

  1. customThen the reaction mixture was evaporated
  2. custompurified by flash chromatography on silica gel with a heptane/ethyl acetate gradient of 0-30% ethyl acetate

Sources & evidence

ORD record
ord-40c154a8db834e39b99fb8cea1c54de0
Source dataset
uspto-grants-2013_02
Patent number
US08367838B2

Reaction notes

Loading…