Triethylamine → Benzyl tert-butyl malonate

HRID 1616997노트

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HRID 1616997 반응식
[C:1]([O:5][C:6](=[O:12])NCC(=O)N)([CH3:4])([CH3:3])[CH3:2].[CH2:13](N(CC)CC)C.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].C([O-])([O-])=O.[Na+].[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:24]([O:23][C:21](=[O:22])[CH2:13][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:12])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 109100641,1-Dimethylethyl N-(2-amino-2-oxoethyl)carbamate

생성물 1

HCID 2736712Benzyl tert-butyl malonate수율 95.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

Carbamoylmethyl-carbamic acid tert-butyl ester (8a; 0.84 g, 4.8 mmol) was dissolved in dichloromethane (10 mL), and added with triethylamine (1.0 mL, 7.2 mmol) and benzyl chloroformate (0.85 g, 0.75 mL, 5.0 mmol) at 0° C. After stirring for 5 min, 4-dimethylaminopyridine (DMAP; 0.32 g, 2.6 mmol) was added slowly with continuous stirring at 0° C. for 1 h. After the reaction is completed, dichloromethane (10 mL) and saturated Na2CO3 solution (10 mL) were added. The organic phase was washed by H2O (10 mL), 1N HCl (20 mL), H2O (20 mL) and saturated NaCl solution (20 mL) separately, and dried over MgSO4 and concentrated under reduced pressure to remove dichloromethane to obtain white solid product 12 (1.15 g; 95%). 1H-NMR (200 MHz) (CDCl3) δ: 7.30˜7.38 (m, 5H, ArH), 5.17 (s, 2H, CO2CH2Ph), 5.02 (br, s, 1H, NHBOC), 3.94 (d, 2H, Gly-H), 1.43 [s, 9H, CO2C(CH3)3]

후처리

  1. stirringwith continuous stirring at 0° C. for 1 h
  2. washThe organic phase was washed by H2O (10 mL), 1N HCl (20 mL), H2O (20 mL) and saturated NaCl solution (20 mL) separately
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto remove dichloromethane

출처 및 근거

ORD 기록
ord-9edbb5fd57f94745ba1d1c2d4ac135e7
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765934B2

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