Diisopropylethylamine → HCID 89851371, 화합물

HRID 627086노트

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HRID 627086 반응식
[CH2:1]([O:4][NH:5][C@H:6]1[CH2:11][NH:10][C@H:9]([C:12]([NH2:14])=[O:13])[CH:8]=[C:7]1[CH3:15])[CH:2]=[CH2:3].[CH2:16]([O:19]N[C@H]1CN[C@@H](C(N)=O)C=C1C)C=C.C(N(CC)C(C)C)(C)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:4][N:5]1[C:16](=[O:19])[N:10]2[CH2:11][C@H:6]1[C:7]([CH3:15])=[CH:8][C@H:9]2[C:12]([NH2:14])=[O:13])[CH:2]=[CH2:3]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 94429Triphosgene2회HCID 89851806(2R,5R)-5-(allyloxyamino)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide2회HCID 89852356(2S,5R)-5-(allyloxyamino)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide

생성물 1

HCID 89851371HCID 89851371, 화합물수율 64.8%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (2S,5R)-5-(allyloxyamino)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide and (2R,5R)-5-(allyloxyamino)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide (Intermediate 22, 0.429 g, 2.03 mmol) and N,N-diisopropylethylamine (1.415 mL, 8.12 mmol) in acetonitrile (170 mL) at 0° C. was added triphosgene (0.241 g, 0.81 mmol) as a solution in acetonitrile (1.5 mL). The triphosgene solution was added at a rate of 0.1 mL/min. Once addition was complete the reaction was warmed to room temperature and stirred over weekend. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded (2S,5R)-6-(allyloxy)-4-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide (0.312 g, 64.8%) as a light yellow oil.

후처리

  1. additionOnce addition
  2. washwashed with saturated sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-73b26f40baac4b7fa0d3ec75c0000028
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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