Triethylamine → HCID 68408428, 화합물

HRID 73588노트

반응식

HRID 73588 반응식
CS([O:5][CH:6]1[CH:11]([CH3:12])[CH2:10][C:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])=[CH:8][CH:7]1[NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=O)=O.C(N(CC)CC)C.C[C:38]([O:41]C(OC(OC(C)(C)C)=O)=O)(C)C>N1C=CC=CC=1>[CH3:12][CH:11]1[CH:6]2[CH:7]([N:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:38](=[O:41])[O:5]2)[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[CH2:10]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 722382272-(Tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl methanesulfonate

생성물 1

HCID 68408428HCID 68408428, 화합물수율 66%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of (+/−)-2-(tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl methanesulfonate (1.0 equiv.) in pyridine (0.2M) was heated in the microwave at 110° C. for 10 min. The orange reaction was then concentrated under vacuo, the crude was dissolved in ethyl acetate and water, the organic phase was dried with sodium sulfate and concentrated under vacuo. The crude material was dissolved in DCM (0.2M), triethylamine (1.8 equiv.) was added, followed by Boc2O (1.2 equiv.). The reaction was stirred for 40 min, then concentrated to dryness. The crude material was purified via silica gel column chromatography eluting with hexane and ethyl acetate (1:1) to afford (+/−)-tert-butyl 7-methyl-5-(3-nitropyridin-4-yl)-2-oxo-3a,6,7,7a-tetrahydrobenzo[d]oxazole-3(2H)-carboxylate as a white foam in 66% yield. LC/MS=376.0 (M+H), LC: 3.424 min.

후처리

  1. customThe orange reaction
  2. concentrationwas then concentrated under vacuo
  3. dissolutionthe crude was dissolved in ethyl acetate
  4. dry with materialwater, the organic phase was dried with sodium sulfate
  5. concentrationconcentrated under vacuo
  6. dissolutionThe crude material was dissolved in DCM (0.2M)
  7. concentrationconcentrated to dryness
  8. customThe crude material was purified via silica gel column chromatography
  9. washeluting with hexane and ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-90ee4eeeb0584aa08a2113204bd5aa4e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829193B2

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