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Potassium Carbonate → Ethyl 2-((2-((tert-butoxycarbonyl)amino)ethyl)((2-(trimethylsilyl)ethoxy)carbonyl)amino)acetate

HRID 1777976
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HRID 1777976 반응식
[C:1](=[O:17])([O-])[O:2][CH2:3][CH:4](N1C(=O)CCC1=O)[Si:5]([CH3:8])([CH3:7])[CH3:6].[C:18]([O:22][C:23]([NH:25][CH2:26][CH2:27][NH:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:24])([CH3:21])([CH3:20])[CH3:19].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.O>[C:18]([O:22][C:23]([NH:25][CH2:26][CH2:27][N:28]([C:1]([O:2][CH2:3][CH2:4][Si:5]([CH3:6])([CH3:7])[CH3:8])=[O:17])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:24])([CH3:21])([CH3:20])[CH3:19]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 4319362Ethyl N-{2-[(tert-butoxycarbonyl)amino]ethyl}glycinate2회HCID 866405022,5-Dioxopyrrolidin-1-yl(2-(trimethylsilyl)ethyl) carbonate

생성물 1

HCID 131734793Ethyl 2-((2-((tert-butoxycarbonyl)amino)ethyl)((2-(trimethylsilyl)ethoxy)carbonyl)amino)acetate

시약·촉매·용매 2

HCID 962Water
용매
HCID 6344Dichloromethane용매

실험 절차

2,5-Dioxopyrrolidin-1-yl(2-(trimethylsilyl)ethyl) carbonate (5.44 g, 20.99 mmol) was added to a mixture of ethyl 2-((2-((tert-butoxycarbonyl)amino)ethyl)amino)acetate (intermediate 126, 4.70 g, 19.08 mmol) and K2CO3 (5.80 g, 42.0 mmol) in DCM (60 ml) and water (30 ml) at room temperature. The reaction mixture was vigorously stirred for 20 h at room temperature, partitioned between saturated aqueous NaHCO3 solution and DCM, the mixture extracted with DCM (2×), the combined organic layers dried over Na2SO4 and evaporated to give the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 6.71 (d, br, 1H), 4.16-3.93 (m, 6H), 3.30-3.21 (m, 2H), 3.09-3.00 (m, 2H), 1.37 (s, 9H), 1.19 (t, 3H), 0.99-0.94 (m, 1H), 0.90-0.85 (m, 1H), 0.05 (s, 9H).

후처리

  1. custompartitioned between saturated aqueous NaHCO3 solution and DCM
  2. extractionthe mixture extracted with DCM (2×)
  3. dry with materialthe combined organic layers dried over Na2SO4
  4. customevaporated

출처 및 근거

ORD 기록
ord-53f9db24ced64b48a7fe2c1e56b11a32
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266883B2

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