Potassium bis(trimethylsilyl)amide → [3-(3-Methyl-4-oxo-5H-2-oxa-1,5,6-triaza-cyclopenta-[a]naphthalen-5-yl)-cyclohexylmethyl]-carbamic acid benzyl ester

HRID 1823268노트

반응식

HRID 1823268 반응식
[CH2:1]([O:8][C:9](=[O:34])[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:19]([C:21]2[C:22]([C:27]3[C:28](Cl)=[N:29][CH:30]=[CH:31][CH:32]=3)=[N:23][O:24][C:25]=2[CH3:26])=[O:20])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:34])[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]2[C:28]3[C:27](=[CH:32][CH:31]=[CH:30][N:29]=3)[C:22]3=[N:23][O:24][C:25]([CH3:26])=[C:21]3[C:19]2=[O:20])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 86592321HCID 86592321, 화합물

생성물 1

HCID 69652675[3-(3-Methyl-4-oxo-5H-2-oxa-1,5,6-triaza-cyclopenta-[a]naphthalen-5-yl)-cyclohexylmethyl]-carbamic acid benzyl ester수율 91.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Dissolve (3-{[3-(2-chloro-pyridin-3-yl)-5-methyl-isoxazole-4-carbonyl]-amino}-cyclohexylmethyl)-carbamic acid benzyl ester (0.74 g, 0.0015 mol) in N,N-dimethylformamide (10 mL) at ambient temperature under a nitrogen atmosphere. Add a solution of potassium bis(trimethylsilyl)amide (0.5 M in toluene, 3.38 mL, 0.0017 mol) and stir for 15 min. at ambient temperature. Quench the dark mixture with water and follow by the addition of solid sodium chloride. Extract with ethyl acetate and wash the combined extracts with water and dry over sodium sulfate. Concentrate and elute over silica gel with methanol/dichloromethane to give the isolation of 0.61 g (89%) of the desired product as a white fluffy solid. MS(ES): (M+1)+ 447.1, 448.1 m/z.

후처리

  1. customQuench the dark mixture with water
  2. additionfollow by the addition of solid sodium chloride
  3. extractionExtract with ethyl acetate
  4. washwash the combined extracts with water
  5. dry with materialdry over sodium sulfate
  6. concentrationConcentrate
  7. washelute over silica gel with methanol/dichloromethane

출처 및 근거

ORD 기록
ord-36302efbbf7a4f1ea7e14ca7a447e77c
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07037921B2

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