Methanesulfonic Acid → (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

HRID 870508ノート

反応式

HRID 870508 の反応式
[CH2:1]([O:8][NH:9][C@H:10]1[CH2:15][NH:14][C@H:13]([C:16]([NH2:18])=[O:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:26]([O:30]C(OC(OC(C)(C)C)=O)=O)(C)(C)C.C(C1NC=CN=1)(C1NC=CN=1)=O.CS(O)(=O)=O.C(=O)([O-])O.[K+]>C1(C)C=CC=CC=1>[CH2:1]([O:8][N:9]1[C:26](=[O:30])[N:14]2[CH2:15][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:16]([NH2:18])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 6

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 516893Potassium BicarbonateHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 71474579(2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxamide

生成物 1

HCID 57389435(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒3 回

反応条件

温度
40 °C

実験手順

(2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxamide (291 mg, 1.17 mmol) was mixed with triethylamine (193 □l, 1.37 mmol) and toluene (2.4 ml) at 20° C. di-t-butyldicarbonate (310 mg, 1.42 mmol) as a solution in toluene (2.0 ml) was added to the reaction mixture, and the mixture was stirred at 40° C. until the reaction was complete. The solution was diluted with toluene (3.9 mL) and carbonyl diimidazole (462 mg, 2.85 mmol) was added and agitation was continued until the reaction was deemed to be complete. Methanesulfonic acid (663 □l, 10.2 mmol) was added and agitation was continued until the reaction was deemed to be complete. After lowering the temperature to 20° C., aqueous potassium hydrogen carbonate (10.2 ml, 1N, 10.2 mmol) was added and the mixture was stirred at 20° C. until the reaction was complete. The aqueous layer was separated and the toluene layer washed with water (3 mL), citric acid (1N, 3 mL) and water (3 mL). The four aqueous washes were twice back-extracted with dichloromethane (2×3 mL). The three organic extracts were combined to give (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide as a solution in toluene and dichloromethane (176 mg, 0.64 mmol, 55%).

後処理

  1. additionwas added to the reaction mixture
  2. additionwas added
  3. customto 20° C.
  4. stirringthe mixture was stirred at 20° C. until the reaction
  5. customThe aqueous layer was separated
  6. washthe toluene layer washed with water (3 mL), citric acid (1N, 3 mL) and water (3 mL)
  7. extractionThe four aqueous washes were twice back-extracted with dichloromethane (2×3 mL)

出典と根拠

ORDレコード
ord-5d2c486837904f81b88036fea2dcffda
出典データセット
uspto-grants-2015_03
特許番号
US08969566B2

反応ノート

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