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1-Hydroxybenzotriazole → N-(3,3-diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide

HRID 2090566
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HRID 2090566 반응식
[CH3:1][O:2][CH2:3][C:4]([CH2:9][O:10][CH3:11])([CH3:8])[C:5]([OH:7])=O.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.[CH2:31]([O:33][CH:34]([O:38][CH2:39][CH3:40])[CH2:35][CH2:36][NH2:37])[CH3:32]>C(Cl)Cl.C1COCC1.C(Cl)CCl>[CH2:31]([O:33][CH:34]([O:38][CH2:39][CH3:40])[CH2:35][CH2:36][NH:37][C:5](=[O:7])[C:4]([CH2:3][O:2][CH3:1])([CH3:8])[CH2:9][O:10][CH3:11])[CH3:32]
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참가 물질

8

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5210291-Amino-3,3-diethoxypropaneHCID 219119313-Methoxy-2-(methoxymethyl)-2-methylpropanoic acid

생성물 1

HCID 86641927N-(3,3-diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide수율 80.7%

시약·촉매·용매 3

HCID 11
1,2-Dichloroethane
용매
HCID 6344Dichloromethane용매2회
HCID 8028Tetrahydrofuran용매

실험 절차

5 g of 3-methoxy-2-methoxymethyl-2-methyl-propionic acid (prepared as described in EP609058) were dissolved in 49 mL of DCM and 12 mL of THF. 11.4 mL of DIPEA, 5.84 g of HOBt, 7.07 g of EDC and 5.45 g of 3,3-diethoxy-propylamine were added sequentially. The mixture was stirred for 23 h at rt, diluted with DCM and washed with sat. NaHCO3. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The resulting crude material was purified by CC using Hept/EtOAc from 3/1 to 0/1 as eluant to yield 7.25 g of N-(3,3-diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide as a yellowish oil.

후처리

  1. washwashed with sat. NaHCO3
  2. dry with materialThe organic phase was dried over anh. Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting crude material was purified by CC

출처 및 근거

ORD 기록
ord-e3183eda780f473aa91094352e5fc363
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08436205B2

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