Sodium Iodide → HCID 10806881, compound

HRID 487428Notes

Reaction equation

HRID 487428 reaction equation
Cl.[C:2]([O:6][C:7](=[O:17])[C@H:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:27][CH:28]([O:32][CH2:33][CH3:34])[O:29][CH2:30][CH3:31]>CN(C)C=O>[C:2]([O:6][C:7](=[O:17])[C@H:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:9][CH2:27][CH:28]([O:32][CH2:33][CH3:34])[O:29][CH2:30][CH3:31])([CH3:5])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 11459563L-Phenylalanine, 1,1-dimethylethyl ester, hydrochloride (1:1)

Product 1

HCID 10806881HCID 10806881, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2.58 g of L-phenylalanine t-butyl ester hydrochloride, 2.76 g of potassium carbonate, 0.1 g of sodium iodide, 2.2 g of 2-bromo-1,1-diethoxyethane and 30 ml of N,N-dimethylformamide was stirred for 24 hours at 100° C. The reaction mixture was poured into ice-water, which was subjected to extraction with hexane. The organic layer was washed with water, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate-hexane=1:4→1:2) to afford 2.2 g of the title compound as a pale yellow oily product.

Workup

  1. extractionwas subjected to extraction with hexane
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate-hexane=1:4→1:2)

Sources & evidence

ORD record
ord-81c89115c77e4bb392832e4888b8bc47
Source dataset
uspto-grants-1994_03
Patent number
US05294713

Reaction notes

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