Sodium Hydroxide → (R)-1-{2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-acetyl}-pyrrolidine-2-carboxylic acid

HRID 1994069노트

반응식

HRID 1994069 반응식
C([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:33])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:24][C:25]=2[CH3:26])[CH:14]=1)=[O:5])C.[OH-].[Na+]>CO>[CH3:26][C:25]1[O:24][C:23]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[N:22][C:21]=1[CH2:20][O:19][C:15]1[CH:14]=[C:13]([CH2:12][C:11]([N:7]2[CH2:8][CH2:9][CH2:10][C@@H:6]2[C:4]([OH:5])=[O:3])=[O:33])[CH:18]=[CH:17][CH:16]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 68675365HCID 68675365, 화합물

생성물 1

HCID 11247155(R)-1-{2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-acetyl}-pyrrolidine-2-carboxylic acid

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of the title B compound, (R)-1-{2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-acetyl}-pyrrolidine-2-carboxylic acid ethyl ester (1.3 g, 2.9 mmol) in 25 mL of methanol at RT is added 1 N aqueous sodium hydroxide (8.7 mL). The mixture is stirred for 20 h and washed with ethyl acetate. The aqueous layer is acidified with 1 N aqueous hydrochloric acid (HCl), extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and concentrated to give an oil. The crude product is purified by flash chromatography (silica gel) eluting with ethyl acetate→ethyl acetate:acetic acid (2:1) to give (R)-1-{2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-acetyl}-pyrrolidine-2-carboxylic acid as a foam: MS m/z 419.1 [M−1]−.

후처리

  1. washwashed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe crude product is purified by flash chromatography (silica gel)
  8. washeluting with ethyl acetate→ethyl acetate:acetic acid (2:1)

출처 및 근거

ORD 기록
ord-6b9e3591fad44e77b69c090521cc4941
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652061B2

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