Triethylamine → {4-[4-(Benzyloxycarbonylamino)phenoxy]pyridin-2-yl}-N-(phenoxycarbonyl)carbamic acid phenyl ester

HRID 2066185ノート

反応式

HRID 2066185 の反応式
[CH2:1]([O:8][C:9](=[O:25])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[CH:19]=2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:31][CH3:32])CC)C.Cl[C:34]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:35]>O1CCCC1>[C:37]1([O:36][C:34](=[O:35])[N:24]([C:20]2[CH:19]=[C:18]([O:17][C:14]3[CH:15]=[CH:16][C:11]([NH:10][C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:25])=[CH:12][CH:13]=3)[CH:23]=[CH:22][N:21]=2)[C:9]([O:25][C:32]2[CH:31]=[CH:4][CH:3]=[CH:2][CH:1]=2)=[O:8])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 59596944[4-(2-Aminopyridin-4-yloxy)phenyl]carbamic acid benzyl ester

生成物 1

HCID 59596983{4-[4-(Benzyloxycarbonylamino)phenoxy]pyridin-2-yl}-N-(phenoxycarbonyl)carbamic acid phenyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of [4-(2-aminopyridin-4-yloxy)phenyl]carbamic acid benzyl ester (500 mg) in tetrahydrofuran (15 ml) were added triethylamine (0.519 ml) and phenyl chloroformate (0.467 ml) while stirring in an ice water bath. The reaction mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned between ethyl acetate (50 ml) and a saturated aqueous solution of sodium hydrogencarbonate (20 ml). The separated organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (20 ml), water (20 ml) and brine (20 ml) in this order, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to provide a crude product of the titled compound as brown foam (935.6 mg).

後処理

  1. stirringThe reaction mixture was stirred at room temperature for 30 min
  2. customThe reaction mixture was partitioned between ethyl acetate (50 ml)
  3. washThe separated organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (20 ml), water (20 ml) and brine (20 ml) in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-a994a932d8b54f6d8600709f5f98ac2d
出典データセット
uspto-grants-2012_10
特許番号
US08288538B2

反応ノート

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