Sodium Iodide → (S)-N-[3-(benzoylamino)-2-oxo-4-phenylbutyl]-L-alanine, 1,1-dimethylethyl ester

HRID 648830Notes

Reaction equation

HRID 648830 reaction equation
Cl[CH2:2][C:3](=[O:21])[C@@H:4]([NH:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[NH2:23][C@H:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH3:25].C(=O)(O)[O-].[Na+].[I-].[Na+]>CN(C)C=O.CCOCC>[C:13]([NH:12][CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](=[O:21])[CH2:2][NH:23][C@H:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH3:25])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 11275390tert-Butyl alaninate hydrochlorideHCID 13339657(3S)-3-Benzoylamino-1-chloro-4-phenyl-2-butanone

Product 1

HCID 56609976(S)-N-[3-(benzoylamino)-2-oxo-4-phenylbutyl]-L-alanine, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of (S)-N-[3-chloro-2-oxo-1-(phenylmethyl)propyl]benzamide 10.0 g., 33.1 mmole) in dimethylformamide (80 ml.) is added L-alanine, 1,1-dimethylethyl ester, hydrochloride (6.0 g., 33.1 mmole), sodium bicarbonate (6.1 g., 72 mmole) and sodium iodide (4.9 g., 33.1 mmole). The resulting solution is stirred overnight at room temperature, poured into ether and washed with water (twice) and 10% sodium bicarbonate. The ether solution is extracted with 1N hydrochloric acid (3×), the combined extracts are made basic by the addition of solid sodium bicarbonate and extracted with ethyl acetate (4×). The organic extracts are combined, dried (MgSO4) and concentrated to give 8.9 g. of pale yellow solid. A portion of this material is recrystallized from ethyl acetate to give (S)-N-[3-(benzoylamino)-2-oxo-4-phenylbutyl]-L-alanine, 1,1-dimethylethyl ester as a white solid; m.p. 106.5°-110°.

Workup

  1. washwashed with water (twice) and 10% sodium bicarbonate
  2. extractionThe ether solution is extracted with 1N hydrochloric acid (3×)
  3. additionthe combined extracts are made basic by the addition of solid sodium bicarbonate
  4. extractionextracted with ethyl acetate (4×)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give 8.9 g
  8. customA portion of this material is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-804c985dc38d4c488e309384c7852386
Source dataset
uspto-grants-1988_04
Patent number
US04736066

Reaction notes

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