Ammonium Chloride → 5-(S)-Azidomethyl-3-[4'-aminocarbonyl-3'-fluorophenyl]oxazolidine-2-one

HRID 351871노트

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HRID 351871 반응식
[N:1]([CH2:4][C@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17](O)=[O:18])=[C:13]([F:20])[CH:12]=2)[CH2:6]1)=[N+:2]=[N-:3].F[P-](F)(F)(F)(F)F.[N:28]1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[Cl-].[NH4+]>CN(C=O)C>[N:1]([CH2:4][C@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([NH2:28])=[O:18])=[C:13]([F:20])[CH:12]=2)[CH2:6]1)=[N+:2]=[N-:3]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 229662095-(S)-azidomethyl-3-(4'-carboxy-3'-fluorophenyl)oxazolidine-2-one

생성물 1

HCID 229662085-(S)-Azidomethyl-3-[4'-aminocarbonyl-3'-fluorophenyl]oxazolidine-2-one수율 91%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 5-(S)-azidomethyl-3-[4′-carboxy-3′-fluorophenyl-]oxazolidine-2-one (3.2 g, 11.4 mmol; prepared as described in Example 3), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluronium hexafluorophosphate (6.5 g, 17.1 mmole) and N,N′-diisopropylethylamine (5.9 g, 7.9 ml , 45.6 mmol) in DMF (12 ml) was stirred at room temperature for 20 min. Ammonium chloride (1.2 g, 22.8 mmol) was added, and the reaction mixture was stirred at r. t. overnight. Most of the solvent was removed under vacuum, and the residue taken up in ethyl acetate and washed twice with 3% aq. citric acid and brine. Organic layer was dried (Na2SO4) and concentrated under vacuum. Crude material was purified by silica gel chromatography eluting with 15% methanol in ethyl acetate to afford a white crystalline product (2.8 g, 91%). HPLC Rt=4.7, MS (m/z): [M+H]+=280.

후처리

  1. customovernight
  2. customMost of the solvent was removed under vacuum
  3. washwashed twice with 3% aq. citric acid and brine
  4. dry with materialOrganic layer was dried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customCrude material was purified by silica gel chromatography
  7. washeluting with 15% methanol in ethyl acetate

출처 및 근거

ORD 기록
ord-d3de7ee8b0b249ff948628d9d81116e6
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743811B2

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