Sodium Bicarbonate → HCID 178501220、化合物

HRID 16706

反応式

HRID 16706 の反応式
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1.O=[CH:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl.C(N(CC)CC)C>[C:19]([O:18][C:17]([NH:16][CH2:15][CH2:14][NH:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:8]1)=[O:23])([CH3:22])([CH3:21])[CH3:20]

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 178501210HCID 178501210、化合物

生成物 1

HCID 178501220HCID 178501220、化合物収率 42%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8471Triethylamine溶媒

実験手順

Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (1.22 g) obtained in Reference Example 2(1) is suspended in dichloromethane (10 ml), and thereto is added triethylamine (1.76 ml) and the mixture is stirred for several minutes. After a solution of t-butyl (2-oxoethyl)carbamate (1.00 g) in dichloromethane (5 ml) and sodium triacetoxy borohydride (1.46 g) are added successively under ice-cooling, the reaction solution is warmed to the room temperature and stirred for 15 hours. Saturated aqueous sodium hydrogen carbonate solution is poured to the reaction solution, and the mixture is extracted with chloroform. The organic layer is dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. A portion (1.71 g) of the resulting residue (2.33 g) is purified by silica gel column chromatography (eluent: chloroform/methanol=10/1) to give methyl trans-4-({2-[(t-butoxycarbonyl)amino]ethyl}amino)-cyclohexanecarboxylate (793 mg).

後処理

  1. temperaturecooling
  2. stirringstirred for 15 hours
  3. extractionthe mixture is extracted with chloroform
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure
  7. customA portion (1.71 g) of the resulting residue (2.33 g) is purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

出典と根拠

ORDレコード
ord-a64d572eb4e34ab18c9971e3e2d6b989
出典データセット
uspto-grants-2010_06
特許番号
US07737161B2

関連ノート

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