Triethylamine → 4-Benzoyl-N-[3-(2-methyl-acryloylamino)-propyl]-benzamide

HRID 514643

반응식

HRID 514643 반응식
[C:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:28])[C:25]([CH3:27])=[CH2:26].C(N(CC)CC)C.[N-]=C=S>CN(C)C=O>[C:1]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:28])[C:25]([CH3:27])=[CH2:26])=[O:15])=[CH:16][CH:17]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 691474-Benzoylbenzoic acidHCID 103750052-Propenamide, N-(3-aminopropyl)-2-methyl-, hydrochloride (1:1)2회HCID 178418790HCID 178418790, 화합물

생성물 1

HCID 99464014-Benzoyl-N-[3-(2-methyl-acryloylamino)-propyl]-benzamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

N-[3-[(4-benzoylphenyl)formamido]propyl]methacrylamide (BPMA, C21H22O3N2, 350.4 g mol−1) monomer was synthesized via reaction of the succinimidyl ester of 4-benzoylbenzoic acid (BP-NHS, 323.3 g mol−1; 81577, Invitrogen) with N-(3-aminopropyl)methacrylamide hydrochloride (APMA, 178.7 g mol−1; 21200, Polysciences, Warrington, Pa.) in the presence of catalytic triethylamine (TEA) in dimethylformamide (DMF). A mixture of the reactants and TEA at 50 mM each in DMF was incubated overnight (18 hrs) at room temperature, centrifuged at 18,000 g for 5 minutes and the pellet discarded. The supernatant was incubated on a tube inverter for 24 hrs with 30 mg isothiocyanate-functionalized (primary amine-reactive) polystyrene beads (538604, Sigma) for every 100 μmol of APMA initially added to the reaction. The mixture was then spun at 18,000 g for 5 minutes and the supernatant passed through a 0.2 μm syringe filter. A 10-fold excess of acetone was added to the filtrate and the mixture dried in vacuo. The BPMA product (white powder) was verified by 1H NMR (400 MHz, d6-DMSO, δ 8.79 (t, 1H), 8.04 (t, 1H), 8.02 (d, 2H), 7.80 (d, 2H), 7.75 (d, 2H), 7.70 (t, 1H), 7.58 (t, 2H), 5.67 (s, 1H), 5.32 (s, 1H), 3.31 (q, 2H), 3.18 (q, 2H), 1.86 (s, 3H), 1.71 (quin, 2H)) and mass spectrometry (ESI, m/z 351.2, C21H22O3N2+H+). 100 mM stocks of BPMA in DMSO were stored at −20° C. until use, and were stable for at least 12 months.

후처리

  1. wait(18 hrs) at room temperature, centrifuged at 18,000 g for 5 minutes
  2. customThe supernatant was incubated on a tube
  3. waitThe mixture was then spun at 18,000 g for 5 minutes
  4. filtrationfilter
  5. additionA 10-fold excess of acetone was added to the filtrate
  6. customthe mixture dried in vacuo
  7. customwere stored at −20° C. until use
  8. waitwere stable for at least 12 months

출처 및 근거

ORD 기록
ord-de89918cf9fb474dbff8a9db07f5bc37
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108195B2

연결된 노트

불러오는 중…