(6R,7R)-2,2-dimethyl-7-phthalimido-1-aza-3-oxabicyclo[4.2.0]octan-8-one → (6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one

HRID 1719303ノート

反応式

HRID 1719303 の反応式
CNN(CCC)NC.[CH3:9][C:10]1([CH3:30])[O:17][CH2:16][CH2:15][C@H:14]2[N:11]1[C:12](=[O:29])[C@@H:13]2[N:18]1C(=O)C2=CC=CC=C2C1=O>CO.ClCCl>[NH2:18][C@H:13]1[C:12](=[O:29])[N:11]2[C@@H:14]1[CH2:15][CH2:16][O:17][C:10]2([CH3:30])[CH3:9]

参加物

5

反応物 2

HCID 53799173(6R,7R)-2,2-dimethyl-7-phthalimido-1-aza-3-oxabicyclo[4.2.0]octan-8-oneHCID 56982963N,N-dimethylaminopropylamine

生成物 1

HCID 12804734(6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one収率 59.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

N,N-Dimethylaminopropylamine (91 μl) was added to a solution of (6R,7R)-2,2-dimethyl-7-phthalimido-1-aza-3-oxabicyclo[4.2.0]octan-8-one (80 mg) in a mixture of methanol (1.4 ml) and dichloromethane (0.7 ml) at 0° C. under a nitrogen atmosphere. The solution was stirred at the same temperature for two hours and left at ambient temperature for 24 hours. The mixture was evaporated and the residue was chromatographed on silica gel (1.5 g; eluting with 3 to 5% methanol in dichloromethane) to give 27 mg (59.5%) of (6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one: IR (CH2Cl2): 3100-3600 (broad) and 1735 cm-1 ; NMR (CDCl3) δ: 1.41 (s, 3H), 1.72 (s, 3H), 1.5-2.1 (m, 4H), 3.34 (ddd, J=2, 5 and 10 Hz, 1H), and 3.7-3.9 (m, 3H).

後処理

  1. waitleft at ambient temperature for 24 hours
  2. customThe mixture was evaporated
  3. customthe residue was chromatographed on silica gel (1.5 g; eluting with 3 to 5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-92732aeb9acb4f2e8effb0e3a62e6cb1
出典データセット
uspto-grants-1985_09
特許番号
US04539152

反応ノート

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