1,1'-Carbonyldiimidazole → (S)-(-)-N-[[3-[4-[1-(Indole-2-carbonyl)-4-piperidinyl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1740150노트

반응식

HRID 1740150 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[O:25]=[C:26]1[N:30]([C:31]2[CH:36]=[CH:35][C:34]([CH:37]3[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)=[C:33]([F:43])[CH:32]=2)[CH2:29][C@H:28]([CH2:44][NH:45][C:46](=[O:48])[CH3:47])[O:27]1>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([N:40]1[CH2:41][CH2:42][CH:37]([C:34]2[CH:35]=[CH:36][C:31]([N:30]3[CH2:29][C@H:28]([CH2:44][NH:45][C:46](=[O:48])[CH3:47])[O:27][C:26]3=[O:25])=[CH:32][C:33]=2[F:43])[CH2:38][CH2:39]1)=[O:12]

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 72899Indole-2-carboxylic acidHCID 15887422(S)-(-)-N-[[2-Oxo-3-[4-(4-piperidinyl)-3-fluorophenyl]-5-oxazolidinyl]methyl]acetamide

생성물 1

HCID 54177616(S)-(-)-N-[[3-[4-[1-(Indole-2-carbonyl)-4-piperidinyl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of indole-2-carboxylic acid (79 mg) and 1,1'-carbonyldiimidazole (80 mg) in dry tetrahydrofuran (2.0 mL) is stirred at ambient temperature for one hour, and a solution of (S)-(-)-N-[[2-oxo-3-[4-(4-piperidinyl)-3-fluorophenyl]-5-oxazolidinyl]methyl]acetamide (EXAMPLE 20, 150 mg) in dry tetrahydrofuran (6.0 mL) is added. The mixture is then stirred at ambient temperature for 19 hours, concentrated under reduced pressure, diluted with methylene chloride (20 mL), washed with saturated aqueous sodium bicarbonate (10 mL), water (10 mL) and saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product which is chromagraphed on silica gel (70-230 mesh, 10 g), eluting with methanol/methylene chloride (7.5/92.5). Pooling and concentration of those fractions with an Rf =0.67 by TLC (methanol/chloroform, 10/90) and recrystallization from chloroform/diethyl ether gives the title compound, mp 223-225° C.

후처리

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with methylene chloride (20 mL)
  3. washwashed with saturated aqueous sodium bicarbonate (10 mL), water (10 mL) and saline (10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product which
  7. washeluting with methanol/methylene chloride (7.5/92.5)
  8. customPooling and concentration of those fractions with an Rf =0.67 by TLC (methanol/chloroform, 10/90) and recrystallization from chloroform/diethyl ether

출처 및 근거

ORD 기록
ord-56d174582bbf4f0698e7519b19c95c0d
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968962

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