Diisopropylethylamine → HCID 67403053, 화합물

HRID 906110노트

반응식

HRID 906110 반응식
C([N:4](CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH3:34][C:35]([O:38][C:39]([C:41]1[CH:49]=[CH:48][C:44]([C:45](O)=[O:46])=[C:43]([N+:50]([O-:52])=[O:51])[CH:42]=1)=[O:40])([CH3:37])[CH3:36]>CN(C)C=O>[NH2:4][C:45]([C:44]1[CH:48]=[CH:49][C:41]([C:39]([O:38][C:35]([CH3:37])([CH3:36])[CH3:34])=[O:40])=[CH:42][C:43]=1[N+:50]([O-:52])=[O:51])=[O:46]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 190761834-(1,1-Dimethylethyl) 2-nitro-1,4-benzenedicarboxylate

생성물 1

HCID 67403053HCID 67403053, 화합물수율 78%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N,N-Diisopropylethylamine (0.41 mL, 2.30 mmol) was added to a mixture of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (321 mg, 0.84 mmol) and 4-{[(1,1-dimethylethyl)oxy]carbonyl}-2-nitrobenzoic acid (prepared according to Gao, Y. et. al WO2001070737) (205 mg, 0.77 mmol) in N,N-dimethylformamide (2 mL), and the reaction mixture was stirred at room temperature for 30 minutes. Ammonia was bubbled into the reaction mixture and stirring was continued for 45 minutes. The reaction mixture was quenched with 0.5M aqueous hydrochloric acid solution (20 mL) and extracted with ethyl acetate (3×20 mL), and the combined extract was washed with water (20 mL), then brine (20 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel flash chromatography (25 to 75% ethyl acetate in hexanes) to give the 1,1-dimethylethyl 4-(aminocarbonyl)-3-nitrobenzoate (160 mg, 78% yield). 1H NMR (400 MHz, CDCl3): 8.55 (s, 1H), 8.25 (d, 1H), 7.64 (d, 1H), 6.51 (br, 1H), 6.26 (br, 1H), 1.61 (s 9H); MS (EI) for C12H14N2O5: 267 (MH+).

후처리

  1. customAmmonia was bubbled into the reaction mixture
  2. stirringstirring
  3. waitwas continued for 45 minutes
  4. customThe reaction mixture was quenched with 0.5M aqueous hydrochloric acid solution (20 mL)
  5. extractionextracted with ethyl acetate (3×20 mL)
  6. extractionthe combined extract
  7. washwas washed with water (20 mL)
  8. dry with materialbrine (20 mL), dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel flash chromatography (25 to 75% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-a3c20a8db8a64bd3988e26aa2d6331d5
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012956B2

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