Tributylphosphine → HCID 22987172, compound

HRID 2304565Notes

Reaction equation

HRID 2304565 reaction equation
[Cl:1][C:2]1[C:11]([CH2:12]O)=[C:10]([CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:15]([O:19][C:20](=[O:33])[CH2:21][C:22]([OH:32])([C:25]1[CH:30]=[CH:29][NH:28][C:27](=[O:31])[CH:26]=1)[CH2:23][CH3:24])([CH3:18])([CH3:17])[CH3:16].C(P(CCCC)CCCC)CCC.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:15]([O:19][C:20](=[O:33])[CH2:21][C:22]([C:25]1[CH:30]=[CH:29][N:28]([CH2:12][C:11]2[C:2]([Cl:1])=[N:3][C:4]3[C:9]([C:10]=2[CH3:14])=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:27](=[O:31])[CH:26]=1)([OH:32])[CH2:23][CH3:24])([CH3:16])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11119047HCID 11119047, compoundHCID 21891949HCID 21891949, compound

Product 1

HCID 22987172HCID 22987172, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture, under an argon atmosphere, of 2-chloro-4-methyl-3-quinolinemethanol (obtained according to 3.c, 2.08 g, 10 mmol), of tert-butyl3-hydroxy-3-(2-oxo-1,2-dihydro-4-pyridinyl)pentanoate (obtained according to 1.h, 2 g, 11 mmol), and tributylphosphine (2.75 ml, 11 mmol) in anhydrous tetrahydrofuran (40 ml) is treated dropwise with diethyl azodicarboxylate (2.6 ml, 15 mmol). The reaction mixture is then agitated at ambient temperature for 6 hours, then concentrated under reduced pressure. The resulting oily residue is taken up in dichloromethane (200 ml) and washed with saturated aqueous ammonium chloride then with saturated aqueous sodium chloride. The organic phase is dried over sodium sulphate then concentrated to 5 ml and acetonitrile is added in order to obtain a white precipitate which is kept at 4° C. for 16 hours. The precipitate is collected by filtration then washed with isopropyl ether in order to produce 1.8 g (39%) of a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with saturated aqueous ammonium chloride
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. concentrationthen concentrated to 5 ml and acetonitrile
  5. additionis added in order
  6. customto obtain a white precipitate which
  7. waitis kept at 4° C. for 16 hours
  8. filtrationThe precipitate is collected by filtration
  9. washthen washed with isopropyl ether in order

Sources & evidence

ORD record
ord-129ce3cefd3c46c992fc6c70a098e348
Source dataset
uspto-grants-2002_08
Patent number
US06436951B1

Reaction notes

Loading…