Ethanolamine → 4-Acetoxybenzyl 2-hydroxyethylcarbamate

HRID 39258

반응식

HRID 39258 반응식
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH2:13]([CH2:15][NH2:16])[OH:14].C(N(CC)CC)C.[C:24](OCC)(=[O:26])C>C(Cl)Cl>[OH:14][CH2:13][CH2:15][NH:16][C:24](=[O:26])[O:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 959064-Acetoxybenzyl alcohol

생성물 1

HCID 583526384-Acetoxybenzyl 2-hydroxyethylcarbamate수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Crude 61 (from 321 mg of 60, max 1.9 mmol) was taken up in 8 mL of CH2Cl2 and the solution was added to a mixture of ethanolamine (140 μL, 2.3 mmol) and triethylamine (540 μL, 3.9 mmol) in 7 mL of CH2Cl2 cooled in an ice bath. The mixture was stirred in the same bath, which was left unmaintained. After 4 h, it was diluted with 100 mL of ethyl acetate and washed with 50 mL of each of 1% HCl in 2/3 saturated brine, 2/3 saturated brine and saturated aqueous NaHCO3 (twice). The organics were dried over Na2SO4 and concentrated in vacuo to furnish 62 (364 mg, 1.44 mmol, 76% over two steps) as a gum. 1H NMR (400 MHz, CDCl3) δ 2.30 (s, 3H), 3.35 (broad q, J=5.2 Hz, 2H), 3.72 (broad q, J=5.2 Hz, 2H), 5.09 (s, 2H), 5.15 (broad s, 1H), 7.07 (d, J=8.5 Hz, 2H), 7.37 (d, J=8.4 Hz, 2H).

후처리

  1. temperaturecooled in an ice bath
  2. waitwas left unmaintained
  3. washwashed with 50 mL of each of 1% HCl in 2/3 saturated brine, 2/3 saturated brine and saturated aqueous NaHCO3 (twice)
  4. dry with materialThe organics were dried over Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ee6c494ac56944f2a62f5faf69baa34c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524691B2

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