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Dicyclohexylcarbodiimide → Benzyl 5-(N-FMOC-L-valyloxy)-4-hydroxy-2-pentenoate

HRID 989996
ノート
印刷プレビュー

反応式

HRID 989996 の反応式
[OH:1][CH:2]([CH2:15][OH:16])[CH:3]=[CH:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[C:17]([NH:34][C@H:35]([C:39](O)=[O:40])[CH:36]([CH3:38])[CH3:37])([O:19][CH2:20][CH:21]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[C:17]([NH:34][C@H:35]([C:39]([O:16][CH2:15][CH:2]([OH:1])[CH:3]=[CH:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])=[O:40])[CH:36]([CH3:37])[CH3:38])([O:19][CH2:20][CH:21]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 688217FMOC-L-valineHCID 54529065Benzyl 4,5-dihydroxy-2-pentenoate

生成物 1

HCID 54039988Benzyl 5-(N-FMOC-L-valyloxy)-4-hydroxy-2-pentenoate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344
Dichloromethane
溶媒
2 回

反応条件

温度
10 °C

実験手順

A mixture of benzyl 4,5-dihydroxy-2-pentenoate (4.4 g, 20 mmole), N-FMOC-L-valine (5.8 g, 17 mmole) and DMAP (0.21 g, 1.7 mmole) in 100 ml dichloromethane was cooled to about 10° C. A solution of DCC (4.2 g, 20 mmole) in 25 ml dichloromethane was added dropwise at the same temperature and the mixture was stirred overnight at room temperature. The mixture was cooled to 5° C. and the urethane was filtered. The filtrate was evaporated under reduced pressure and the product was isolated by silica gel column chromatography. Yield: 6.6 g=71%

後処理

  1. temperatureThe mixture was cooled to 5° C.
  2. filtrationthe urethane was filtered
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe product was isolated by silica gel column chromatography

出典と根拠

ORDレコード
ord-89a89f6a177147aba1c45018eb0c03db
出典データセット
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06458772B1

反応ノート

読み込み中…

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