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

HRID 1888352노트

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HRID 1888352 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

HCID 104021382-Benzyloxycarbamoyl-4-methylpentanoic acid ethyl ester수율 94.5%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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 hydroxylamine (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.

후처리

  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

출처 및 근거

ORD 기록
ord-d685b7da514c457791bf5c62b668595e
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501798B2

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