Water → HCID 178453881、化合物

HRID 899064

反応式

HRID 899064 の反応式
C([Li])CCC.[C:6]([O:10][C:11](=[O:32])[CH:12](P(OCC)(OCC)=O)[CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])([CH3:9])([CH3:8])[CH3:7].[C:33]([O:37][C:38](=[O:48])[NH:39][C@H:40]1[CH2:45][CH2:44][C@H:43]([CH:46]=O)[CH2:42][CH2:41]1)([CH3:36])([CH3:35])[CH3:34].O>C1COCC1>[C:6]([O:10][C:11](=[O:32])[C:12](=[CH:46][C@H:43]1[CH2:42][CH2:41][C@H:40]([NH:39][C:38]([O:37][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:48])[CH2:45][CH2:44]1)[CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])([CH3:7])([CH3:8])[CH3:9]

参加物

6

反応物 4

HCID 962WaterHCID 537909152-(Diethoxy-phosphoryl)-succinic acid 4-benzyl ester 1-tert-butyl esterHCID 178418339ButyllithiumHCID 178453955HCID 178453955、化合物

生成物 1

HCID 178453881HCID 178453881、化合物収率 40.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Butyllithium (1.6 M in hexane, 5.0 ml, 8.00 mmol) was added dropwise to a solution of 2-(diethoxy-phosphoryl)-succinic acid 4-benzyl ester 1-tert-butyl ester (3.21 g, 8.00 mmol) in THF (25 mL) at 0° C. under nitrogen. After stirring at 0° C. for 1 h, the solution was transferred to a solution of trans-(4-Formyl-cyclohexyl)-carbamic acid tert-butyl ester (1.30 g, 5.72 mmol) in THF (10 mL). The resulting mixture was stirred at 0° C. for 1 h and at room temperature overnight. Water was added and the product extracted with CH2Cl2. The organic phase was dried and concentrated under reduced pressure. Flash chromatography (hexane/EtOAc, 80:20) gave trans-2-(4-tert-Butoxycarbonylamino-cyclohexylmethylene)-succinic acid 4-benzyl ester 1-tert-butyl ester (1.10 g).

後処理

  1. stirringThe resulting mixture was stirred at 0° C. for 1 h and at room temperature overnight
  2. extractionthe product extracted with CH2Cl2
  3. customThe organic phase was dried
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ba365c8828124290bc4c4dc3f18ab655
出典データセット
uspto-grants-2008_04
特許番号
US07354895B1

関連ノート

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