Diisopropylethylamine → (2S,5R)-6-(allyloxy)-2-(methoxymethyl)-N,N-dimethyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-4-carboxamide

HRID 627170노트

반응식

HRID 627170 반응식
[CH2:1]([O:4][NH:5][C@@H:6]1[C:11]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])=[CH:10][C@@H:9]([CH2:17][O:18][CH3:19])[NH:8][CH2:7]1)[CH:2]=[CH2:3].CCN(C(C)C)C(C)C.Cl[C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl>C(#N)C>[CH2:1]([O:4][N:5]1[C:30](=[O:32])[N:8]2[CH2:7][C@H:6]1[C:11]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])=[CH:10][C@H:9]2[CH2:17][O:18][CH3:19])[CH:2]=[CH2:3]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 89852322(3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide2회

생성물 1

HCID 89852352(2S,5R)-6-(allyloxy)-2-(methoxymethyl)-N,N-dimethyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-4-carboxamide수율 206.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

A solution of (3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide (Intermediate 142, 725 mg, 2.69 mmol) and Hunig's Base (1.880 mL, 10.77 mmol) in acetonitrile (350 mL) was cooled to below 0° C. in an ice-salt bath and then a solution of triphosgene (320 mg, 1.08 mmol) in ACN (22 mL) was added at a rate of 0.1 mL/min. The reaction was stirred overnight at rt. Upon completion of the reaction, the solvents were removed and the crude mixture was redissolved in EtOAc, washed with sat. NaHCO3 and brine, dried over MgSO4, filtered and concentrated to obtain the desired product (658 mg, 83%) as a pale yellow oil.

후처리

  1. customUpon completion of the reaction
  2. customthe solvents were removed
  3. dissolutionthe crude mixture was redissolved in EtOAc
  4. washwashed with sat. NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d4551fc08ac84952aed435d11e22faf1
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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