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

HRID 648830ノート

反応式

HRID 648830 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-804c985dc38d4c488e309384c7852386
出典データセット
uspto-grants-1988_04
特許番号
US04736066

反応ノート

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