Sodium Iodide → 2-Methyl-2-[(1-phenethyloxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-propionic acid methyl ester

HRID 874744Notes

Reaction equation

HRID 874744 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[C:11]=1[OH:20])=[O:9])([CH3:6])[CH3:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[I-].[Na+]>CN(C)C=O.O.C(OCC)C>[CH3:1][O:2][C:3](=[O:21])[C:4]([CH3:6])([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[C:11]=1[O:20][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:9])[CH3:5]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 7666Phenethyl bromideHCID 10796Cesium carbonateHCID 57912188HCID 57912188, compound

Product 1

HCID 688447242-Methyl-2-[(1-phenethyloxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-propionic acid methyl esterYield 63.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

80 mg 2-[(1-hydroxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-2-methyl-pro-pionic acid methyl ester, 224 mg cesium carbonate, 61 mg of (2-bromoethyl)-benzene and 4 mg sodium iodide were dissolved in 5 ml of N,N-dimethylformamide and stirred at 80° C. for 6 h. 10 ml of diethyl ether and 10 ml of water were added to the reaction. The organic layer was separated and washed again with 10 ml of water. It was then dried over magnesium sulphate, filtered and concentrated in vacuo. Purification by flash chromatography (silica, heptanes/ethyl acetate) afforded 69 mg of 2-methyl-2-[(1-phenethyloxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-propionic acid methyl ester.

Workup

  1. customThe organic layer was separated
  2. washwashed again with 10 ml of water
  3. dry with materialIt was then dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (silica, heptanes/ethyl acetate)

Sources & evidence

ORD record
ord-c1ada699085743b69283b672e455f424
Source dataset
uspto-grants-2015_03
Patent number
US08980938B2

Reaction notes

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