(S)-(-)-N-[[3-[4-[1-[(Benzyloxy)acetyl]-4-piperidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide → (S)-(-)-N-[[3-[4-[1-(Hydroxyacetyl)-4-piperidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1740143노트

반응식

HRID 1740143 반응식
C([O:8][CH2:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:28][C@H:27]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[O:26][C:25]3=[O:34])=[CH:20][CH:19]=2)[CH2:14][CH2:13]1)=[O:11])C1C=CC=CC=1>CO.[Pd]>[OH:8][CH2:9][C:10]([N:12]1[CH2:13][CH2:14][CH:15]([C:18]2[CH:19]=[CH:20][C:21]([N:24]3[CH2:28][C@H:27]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[O:26][C:25]3=[O:34])=[CH:22][CH:23]=2)[CH2:16][CH2:17]1)=[O:11]

참가 물질

4

반응물 1

HCID 53881294(S)-(-)-N-[[3-[4-[1-[(Benzyloxy)acetyl]-4-piperidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

생성물 1

HCID 54329358(S)-(-)-N-[[3-[4-[1-(Hydroxyacetyl)-4-piperidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A mixture of (S)-(-)-N-[[3-[4-[1-[(benzyloxy)acetyl]-4-piperidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (EXAMPLE 18, 207 mg) and 10% palladium-on-carbon (100 mg) in methanol (9 mL) is shaken on a Parr apparatus under a hydrogen atmosphere at 40 psi for 20 hours, the catalyst is removed by filtration through Celite and the filtrate is concentrated under reduced pressure to give the crude product which is chromatographed on silica gel (230-400 mesh, 20 g), eluting with a gradient of methanol/methylene chloride (5/95-10/90). Pooling and concentration of those fractions with an Rf =0.26 by TLC (methanol/chloroform, 10/90) and recrystallization from methylene chloride/diethyl ether gives the title compound, mp 155-157° C.

후처리

  1. customthe catalyst is removed by filtration through Celite
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customto give the crude product which
  4. customis chromatographed on silica gel (230-400 mesh, 20 g)
  5. washeluting with a gradient of methanol/methylene chloride (5/95-10/90)
  6. customPooling and concentration of those fractions with an Rf =0.26 by TLC (methanol/chloroform, 10/90) and recrystallization from methylene chloride/diethyl ether

출처 및 근거

ORD 기록
ord-be7a716b3e8d49a08b472c7f00e45424
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968962

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