Triethylamine → (9H-fluoren-9-yl)methyl prop-2-yn-1-ylcarbamate

HRID 1057068노트

반응식

HRID 1057068 반응식
[C:1](Cl)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].[CH2:19]([NH2:22])[C:20]#[CH:21].C(N(CC)CC)C>C(Cl)Cl.CCCCCC>[CH2:19]([NH:22][C:1](=[O:2])[O:3][CH2:4][CH:5]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:20]#[CH:21]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 343679-Fluorenylmethyl chloroformateHCID 239041Propargylamine

생성물 1

HCID 10084877(9H-fluoren-9-yl)methyl prop-2-yn-1-ylcarbamate수율 95.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8058Hexane용매

실험 절차

A solution of Fmoc chloride (25.00 g, 96.64 mmol, 1.05 eq.) in DCM (150 mL) was added dropwise to a solution of propargylamine 8 (5.89 mL, 92.04 mmol, 1.0 eq.) and triethylamine (15.4 mL, 110.4 mmol, 1.2 eq.) in DCM (200 mL) at −78° C. The reaction mixture was allowed to stir at room temperature, and after 16 hours the solution was washed with water (300 mL), 0.1 N aqueous citric acid (300 mL), saturated aqueous NaHCO3 (300 mL) and brine (200 mL). The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure to provide an amorphous white powder. Sonication in cold hexane (200 mL) followed by filtration afforded the product as a white solid (24.316 g, 95%). LC/MS (2.758 min (ES+)). m/z: 300.0 [M+Na]+. 1H NMR (400 MHz, CDCl3) δ 7.74 (d, 2H, J=7.6 Hz), 7.57 (d, 2H, J=7.4 Hz), 7.41-7.37 (m, 2H), 7.30 (dt, 2H, J=7.5, 1.2 Hz), 4.93 (br s, 1H), 4.41 (d, 2H, J=6.9 Hz), 4.21 (t, 1H, J=6.4 Hz), 3.99 (d, 2H, J=3.3 Hz), 2.24 (t, 1H, J=2.5 Hz).

후처리

  1. washafter 16 hours the solution was washed with water (300 mL), 0.1 N aqueous citric acid (300 mL), saturated aqueous NaHCO3 (300 mL) and brine (200 mL)
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto provide an amorphous white powder
  6. filtrationfollowed by filtration

출처 및 근거

ORD 기록
ord-9cc1e302c8c94ad695142d7d98178116
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399073B2

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