Triphenylphosphine → HCID 57602497, compound

HRID 1787921Notes

Reaction equation

HRID 1787921 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][C:20]=3[OH:28])=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:48]([NH:55][CH2:56][CH2:57]O)([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:48]([NH:55][CH2:56][CH2:57][O:28][C:20]1[CH:21]=[C:22]([CH:25]([CH3:26])[CH3:27])[CH:23]=[CH:24][C:19]=1[CH2:18][NH:17][C:12]1[C:11]([C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:10])=[CH:16][CH:15]=[CH:14][N:13]=1)([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 57602503HCID 57602503, compound

Product 1

HCID 57602497HCID 57602497, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-(4-chlorophenyl)-2-[2-hydroxy-4-isopropylbenzylamino]pyridine-3-carboxamide (0.050 g, 0.13 mmol), triphenylphosphine (0.033 g, 0.13 mmol) and N-Boc-ethanolamine (0.018 mg, 0.11 mmol) in 0.3 mL tetrahydrofuran at −10° C. was added a solution of diethyl azodicarboxylate (0.02 mL, 0.13 mmol) in 0.3 mL tetrahydrofuran. The reaction was stirred at room temperature for 3 days. The solvent was removed in vacuo; and the crude material was purified by chromatography over silica, using an eluent gradient of 20-30% ethyl acetate in hexanes, to afford the named product (0.02 g, 30%).

Workup

  1. customThe solvent was removed in vacuo
  2. customand the crude material was purified by chromatography over silica

Sources & evidence

ORD record
ord-7c19fc9f6df5401bb5c66e1c1807f9a4
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

Loading…