Lithium Hydroxide → (S)-2-ethoxy-3-(3'-{[methyl-(1-phenylmethanoyl)amino]methyl}biphenyl-4-yl)propionic acid

HRID 584911노트

반응식

HRID 584911 반응식
C([C@H]1COC(=O)N1C(=O)[C@@H:15]([O:40][CH2:41][CH3:42])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]([CH3:39])[C:31](=[O:38])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:24]=2)=[CH:19][CH:18]=1)C1C=CC=CC=1.C1[CH2:48][O:47]CC1.[OH-:49].[Li+]>O>[CH2:41]([O:40][C@@H:15]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]([CH3:39])[C:31]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[O:38])[CH:24]=2)=[CH:21][CH:22]=1)[C:48]([OH:47])=[O:49])[CH3:42]

참가 물질

5

반응물 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 69694199N-{4'-[(S)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-2-ethoxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamide

생성물 1

HCID 10273463(S)-2-ethoxy-3-(3'-{[methyl-(1-phenylmethanoyl)amino]methyl}biphenyl-4-yl)propionic acid수율 47%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

600 mg (1 mmol) of N-{4′-[(S)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-2-ethoxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamide and 10 ml of THF are introduced into a round-bottomed flask. At 0° C., 4.2 ml (2 mmol) of an aqueous lithium hydroxide solution (0.5M) are added and the mixture is stirred for one hour. The reaction medium is poured into water, acidified to pH 1 and extracted with ethyl acetate, and the organic phase is separated out after settling of the phases has taken place, dried over magnesium sulfate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (50/50). 200 mg (47%) of (S)-2-ethoxy-3-(3′-{[methyl-(1-phenylmethanoyl)amino]methyl}biphenyl-4-yl)propionic acid, with a melting point of 53-54° C., are obtained.

후처리

  1. extractionextracted with ethyl acetate
  2. customthe organic phase is separated out
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a mixture of heptane and ethyl acetate (50/50)

출처 및 근거

ORD 기록
ord-5d4a5717dac2420fa4c5ecc8d083c066
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06927228B2

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