Triethylamine → HCID 19801627, compound

HRID 1646175Notes

Reaction equation

HRID 1646175 reaction equation
[CH2:1]([O:3][P:4]([O-:8])[O:5][CH2:6][CH3:7])[CH3:2].C(N(CC)CC)C.Br[C:17]1[CH:18]=[C:19]([CH2:23][NH:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:20]=[CH:21][CH:22]=1>C1(C)C=CC=CC=1.[Pd].C(OCC)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][P:4]([O:5][CH2:6][CH3:7])([C:21]1[CH:20]=[C:19]([CH2:23][NH:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:18]=[CH:17][CH:22]=1)=[O:8])[CH3:2]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 19801606HCID 19801606, compound

Product 1

HCID 19801627HCID 19801627, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of diethylphosphite (1 ml, 6.75 mmol) and triethylamine (5 ml) is stirred under a nitrogen atmosphere and then treated with tetrakis (triphenylphosphine) palladium (0) (0.4 g). A solution of methyl N-[(3-bromophenyl)methyl]glycinate (Example C) (1.62 g, 6.28 mmol) in toluene (10 ml) is degassed in vacuo, added to the palladium catalyst mixture, and the reaction vessel immersed in a 105° C. oil bath for 17 hours. The reaction mixture is cooled to room temperature and diluted with diethyl ether. An insoluble precipitate is removed by filtration and the filtrate evaporated to give a yellow residue. The product is purified by chromatography on silica gel (0-5% methanol in chloroform as eluant). 1H-NMR: 4H, m, 7.9-7.3 ppm; 4H, m, 4.25-3.95; 2H, s, 3.8; 3H, s, 3.7; 2H, s, 3.4; 6H, t, 1.25.

Workup

  1. customimmersed in a 105° C.
  2. customfor 17 hours
  3. customAn insoluble precipitate is removed by filtration
  4. customthe filtrate evaporated
  5. customto give a yellow residue
  6. customThe product is purified by chromatography on silica gel (0-5% methanol in chloroform as eluant)

Sources & evidence

ORD record
ord-6d22ef18de6d49dea01e88895f4b5df1
Source dataset
uspto-grants-1993_01
Patent number
US05179085

Reaction notes

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