Acetonitrile → 7-[2-(t-Butoxycarbonyl)-8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-1-cyclopropyl-5-amino-6,8-difluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

HRID 428461

反応式

HRID 428461 の反応式
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([NH2:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:22][O:23][N:24]=[C:25]1[C:29]2([CH2:32][N:31]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:30]2)[CH2:28][NH:27][CH2:26]1.C(#N)C.C(N(CC)CC)C>CN(C)C=O>[C:36]([O:35][C:33]([N:31]1[CH2:32][C:29]2([C:25](=[N:24][O:23][CH3:22])[CH2:26][N:27]([C:11]3[C:12]([F:14])=[C:13]4[C:8]([C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5][N:4]4[CH:1]4[CH2:2][CH2:3]4)=[C:9]([NH2:17])[C:10]=3[F:16])[CH2:28]2)[CH2:30]1)=[O:34])([CH3:39])([CH3:38])[CH3:37]

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 545476562,6-Diazaspiro[3.4]octane-2-carboxylic acid, 8-(methoxyimino)-, 1,1-dimethylethyl ester

生成物 1

HCID 543496637-[2-(t-Butoxycarbonyl)-8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-1-cyclopropyl-5-amino-6,8-difluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid収率 31.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

750 mg of 1-cyclopropyl-5-amino-6,7,8-trifluoro-4-oxo-1,4-dihydro-3-quinoline-carboxylic acid, 1.05 g of t-butyl 8-(methoxyimino)-2,6-diazaspiro[3,4]octane-2-carboxylate and 4 g of Amberlite® IRA-420 were added to 20 ml of acetonitrile and thereto 2 ml of triethylamine was added by dropping. The mixture was refluxed for 5 days and then 2 ml of dimethylformamide was added thereto. The resulting mixture was stirred for 1 hour and thus precipitated solid was filtered off. The filtrate was concentrated under the reduced pressure and then to the resulting residue 10 ml of acetonitrile was added and stirred for 1 hour. The precipitated solid was filtered and dried to give 420 mg of the titled compound(yield: 30.9%).

後処理

  1. temperatureThe mixture was refluxed for 5 days
  2. filtrationthus precipitated solid was filtered off
  3. concentrationThe filtrate was concentrated under the reduced pressure
  4. additionto the resulting residue 10 ml of acetonitrile was added
  5. stirringstirred for 1 hour
  6. filtrationThe precipitated solid was filtered
  7. customdried

出典と根拠

ORDレコード
ord-d7fd68198c9d4954a1470470f7d25f9d
出典データセット
uspto-grants-2001_11
特許番号
US06313299B1

関連ノート

読み込み中…