Tetrahydrofuran → (R)-(-)-N-Carbobenzyloxy-3-[2-fluoro-4-[5-hydroxymethyl-2-oxo-3-oxazolidinyl]phenyl]azetidine

HRID 1004842노트

반응식

HRID 1004842 반응식
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[C:6]([N:16]1[CH2:19][CH:18]([C:20]2[CH:36]=[CH:35][C:23]([NH:24][C:25]([O:27][CH2:28][C:29]3C=CC=CC=3)=[O:26])=[CH:22][C:21]=2[F:37])[CH2:17]1)([O:8][CH2:9][C:10]1[CH:15]=CC=CC=1)=[O:7].C1C[O:41][CH2:40]C1>CCCCCC>[C:6]([N:16]1[CH2:19][CH:18]([C:20]2[CH:36]=[CH:35][C:23]([N:24]3[CH2:29][C@H:28]([CH2:40][OH:41])[O:27][C:25]3=[O:26])=[CH:22][C:21]=2[F:37])[CH2:17]1)([O:8][CH2:9][C:10]1[CH:15]=[CH:4][CH:3]=[CH:2][CH:1]=1)=[O:7]

참가 물질

5

반응물 3

HCID 8028Tetrahydrofuran2회HCID 22625683N-Carbobenzyloxy-3-(N-carbobenzyloxy-3-fluoroanilin-4-yl)azetidineHCID 178418339Butyllithium

생성물 1

HCID 21967688(R)-(-)-N-Carbobenzyloxy-3-[2-fluoro-4-[5-hydroxymethyl-2-oxo-3-oxazolidinyl]phenyl]azetidine

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

n-Butyllithium (5.25 mL of a 1.6 M solution in hexane, 8.40 mmol) was added dropwise to a stirred solution of N-carbobenzyloxy-3-(N-carbobenzyloxy-3-fluoroanilin-4-yl)azetidine (Example 81, Step 4, 3.63 g, 8.36 mmol) at -78° under nitrogen in dry THF (30 mL), then stirred for 2 hr. A solution of R-glycidyl butyrate (1.21 g, 8.40 mmol) in dry THF (3.0 mL) was added and the cooling bath removed after 15 min. After 18 hr, the solvent was removed and the residue partitioned between ethyl acetate (150 mL) and saturated ammonium chloride solution (50 mL). The organic layer was washed with water (50 mL) and brine (50 mL), dried over magnesium sulfate, filtered and evaporated leaving an amber oil. Chromatography over silica gel (150 g, 40-60 lim) eluting with 2-5% methanol-chloroform gave the title compound as a sticky foam. FAB-HRMS: theory 401.1513 (M+1); meas 401.1521.

후처리

  1. customthe cooling bath removed after 15 min
  2. waitAfter 18 hr
  3. customthe solvent was removed
  4. customthe residue partitioned between ethyl acetate (150 mL) and saturated ammonium chloride solution (50 mL)
  5. washThe organic layer was washed with water (50 mL) and brine (50 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customleaving an amber oil
  10. washChromatography over silica gel (150 g, 40-60 lim) eluting with 2-5% methanol-chloroform

출처 및 근거

ORD 기록
ord-8f9b361818b44553a1597155e2a924a9
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06051716

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