N,O-Dimethylhydroxylamine → HCID 86671822, 화합물

HRID 536992노트

반응식

HRID 536992 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][NH:17][O:18][CH3:19].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1([C:13](=[O:15])[N:17]([O:18][CH3:19])[CH3:16])[CH2:10][CH2:11][CH2:12]1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 14232N,O-DimethylhydroxylamineHCID 81531DiisopropylethylamineHCID 1512646Cyclobutanecarboxylic acid, 1-(((1,1-dimethylethoxy)carbonyl)amino)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 86671822HCID 86671822, 화합물수율 87%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-tert-butoxycarbonylamino-cyclobutanecarboxylic acid (3 g, 13.94 mmol) in dry DMF (50 mL) was added N,O-dimethylhydroxylamine x HCl (1.36 g, 13.94 mmol) and DIEA (9.21 mL, 55.75 mmol). The reaction flask was cooled to 0° C. and after 10 minutes HATU (5.30 g, 13.94 mmol) was added to the solution (which turned yellow on addition). After 2 hrs the DMF was removed by rotary evaporation at reduced pressure. The residue was dissolved in EtOAc (100 mL) and washed twice with 10% citric acid (aq) and saturated NaHCO3(aq) solution. The organic phase was dried with Na2SO4, filtered and evaporated on silica. The product was purified by flash chromatography (heptane: ethyl acetate (1:1) to give the product as a colourless oil that slowly crystallizes (3.13 g) in 87% yield.

후처리

  1. additionwas added to the solution (which turned yellow on addition)
  2. customAfter 2 hrs the DMF was removed by rotary evaporation at reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (100 mL)
  4. washwashed twice with 10% citric acid (aq) and saturated NaHCO3(aq) solution
  5. dry with materialThe organic phase was dried with Na2SO4
  6. filtrationfiltered
  7. customevaporated on silica
  8. customThe product was purified by flash chromatography (heptane: ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-cc2b44842334443cae2b9a779cdf8194
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859605B2

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