HOAc dioxane → (S)-2-[[(S)-2-(Acetoxyacetyl)-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide

HRID 1735395

반응식

HRID 1735395 반응식
[N+](=[CH:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:12])=[O:5])=[N-].[C:28]([OH:31])(=[O:30])[CH3:29].O1CCOCC1>>[C:28]([O:31][CH2:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:12])=[O:5])(=[O:30])[CH3:29]

참가 물질

3

반응물 2

HCID 22565020HOAc dioxaneHCID 54423239(S)-2-[[(S)-2-(Diazoacetyl)-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide

생성물 1

HCID 15389023(S)-2-[[(S)-2-(Acetoxyacetyl)-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide

반응 조건

온도
100 °C

실험 절차

(S)-2-[[(S)-2-(Diazoacetyl)-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide (3.63 g) was dissolved in acetic acid-1,4-dioxane (1:1, 36 ml), and the mixture was heated at 100° C. for 10 minutes. The reaction mixture was concentrated, added with methylene chloride, washed with a saturated aqueous solution of sodium bicarbonate and water in order, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent: chloroform-methanol) to give the title compound (1.47 g) (see Table 1).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additionadded with methylene chloride
  3. washwashed with a saturated aqueous solution of sodium bicarbonate and water in order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent: chloroform-methanol)

출처 및 근거

ORD 기록
ord-22e1f570dc3c4e3b92ba19b42c1e9362
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05536737

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