Triethylamine → 2-Benzyloxycarbamoyl-4-methylpentanoic acid ethyl ester

HRID 1669545ノート

反応式

HRID 1669545 の反応式
[CH2:1]([O:3][C:4](=[O:13])[CH:5]([CH2:9][CH:10]([CH3:12])[CH3:11])[C:6]([OH:8])=O)[CH3:2].[CH2:14](NO)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1C=CC2[N:31]([OH:32])N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:13])[CH:5]([C:6](=[O:8])[NH:31][O:32][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:9][CH:10]([CH3:12])[CH3:11])[CH3:2]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2794173BenzylhydroxylamineHCID 101039412-(Ethoxycarbonyl)-4-methylpentanoic acid

生成物 1

HCID 104021382-Benzyloxycarbamoyl-4-methylpentanoic acid ethyl ester収率 94.5%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Intermediate (3a) (40.3 g, 214 mmol, 1.0 eq) was dissolved into 800 mL DCM and 900 mL THF and the solution was cooled to 0° C. To this was added benzyl hydroxyl amine (34.2 g, 214 mmol, 1.0 eq) followed by HOBt (28.9 g, 214 mmol, 1.0 eq). The mixture was stirred for 5 minutes, then DCC (44.1 g, 214 mmol, 1.0 eq) was added, followed by triethylamine (33.4 mL, 240 mmol, 1.1 eq). The mixture was warmed to room temperature and stirred overnight. The solid was filtered and the filtrate was concentrated. The material was redissolved in 1000 mL EtOAc and washed with 500 mL 1N HCl, 600 mL saturated aq. bicarbonate, dried over MgSO4, filtered. and evaporated to yield intermediate (3b) (59.3 g) as a semisolid. MS m/z: [M+H+] calcd for C16H23NO4 294.2; found 294.2.

後処理

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred overnight
  3. filtrationThe solid was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe material was redissolved in 1000 mL EtOAc
  6. washwashed with 500 mL 1N HCl, 600 mL saturated aq. bicarbonate
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customand evaporated

出典と根拠

ORDレコード
ord-1f4eb9b91c304f3faab11f9d0fe7ec9c
出典データセット
uspto-grants-2011_08
特許番号
US07989484B2

反応ノート

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