Triethylamine → n-[2-(4-Methyl-2-nitro-benzenesulfonylamino)-ethyl]-glycine ethyl ester

HRID 1794934노트

반응식

HRID 1794934 반응식
Cl.Cl.[CH2:3]([O:5][C:6](=[O:12])[CH2:7][NH:8][CH2:9][CH2:10][NH2:11])[CH3:4].C(N(CC)CC)C.[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[C:23]([N+:31]([O-:33])=[O:32])[CH:22]=1>ClCCl>[CH2:3]([O:5][C:6](=[O:12])[CH2:7][NH:8][CH2:9][CH2:10][NH:11][S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:20])=[CH:22][C:23]=1[N+:31]([O-:33])=[O:32])(=[O:28])=[O:29])[CH3:4]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 1046892-Nitro-p-toluenesulphonyl chlorideHCID 74889816N-beta-Aminoethyl-gly-oet 2hcl

생성물 1

HCID 22222384n-[2-(4-Methyl-2-nitro-benzenesulfonylamino)-ethyl]-glycine ethyl ester수율 92.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of N-(2-aminoethyl)-glycine ethyl ester 2HCl (1.10 g, 5.0 mmol), prepared as described by Will (D. W. Will et al., Tetrahedron, 1995, 51, 12069–12802.), in dichloromethane (50 mL) was slowly added triethylamine (2.02 g, 20 mmol) at room temperature. Then 4-methyl-2-nitro-benzenesulfonyl chloride (1.19 g 5.0 mmol) in dichloromethane (10 mL) was added to the reaction mixture at room temperature for 5 min. The resulting reaction mixture was stirred for additional 2 h. at room temperature and washed with water (30 mL). The organic layer was dried over MgSO4 and filtered. The filtrate was evaporated in vacuo to give desired product (1.60 g, 92%) as a solid. 1H-NMR (500 MHz; DMSO-d6) δ 7.87 (d, 1H), 7.81 (s, 1H), 7.66 (d, 1H), 4.06 (q, 2H), 3.24 (s, 2H), 2.91 (t, 2H), 2.57 (t, 2H), 2.44 (s, 3H), 1.17 (t, 3H).

후처리

  1. customat room temperature
  2. customThe resulting reaction mixture
  3. washwashed with water (30 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo

출처 및 근거

ORD 기록
ord-197102b53369420e9412261001138352
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022851B2

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