Diphosgene → (6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-yl 3-(dimethylamino)propyl(methyl)carbamate

HRID 530166

반응식

HRID 530166 반응식
[CH2:1]([CH:11]([CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:12]([OH:23])[CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].O=C(Cl)[O:36][C:37](Cl)(Cl)Cl.[CH3:42][N:43]([CH3:49])[CH2:44][CH2:45][CH2:46][NH:47][CH3:48]>C(OCC)C>[CH3:42][N:43]([CH3:49])[CH2:44][CH2:45][CH2:46][N:47]([CH3:48])[C:37](=[O:36])[O:23][CH:12]([CH:11]([CH2:1][CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

참가 물질

5

반응물 3

HCID 10426DiphosgeneHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 89775018(6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-ol

생성물 1

HCID 89775024(6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-yl 3-(dimethylamino)propyl(methyl)carbamate수율 23%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
-15 °C

실험 절차

A solution of (6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-ol 8 (0.5 g, 1.1 mmol) in anhydrous diethyl ether (10 mL) was added slowly a solution of diphosgene (0.2 mL, 1.8 mmol) in anhydrous diethyl ether cooled to approximately −15° C. The solution was stirred for 1 hour then N,N,N′-trimethyl-1,3-propanediamine (1.3 mL, 8.7 mmol) was added at −15° C. The solution was warmed to room temperature, stirred for 1 hour, and then filtered to remove the ammonium salts and urea. The diethyl ether filtrate was concentrated in vacuo to dryness. The residue was purified by column chromatography (100% ethyl acetate) to afford (6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-yl 3-(dimethylamino)propyl(methyl)carbamate 23 as a colorless oil (0.15 g, 23%), 1H NMR (400 MHz, CDCl3) δ 5.41-5.29 (m, 6H), 4.85-4.77 (m, 1H), 3.35-3.21 (m, 2H), 2.93-2.81 (m, 3H), 2.31-2.17 (m, 8H), 2.08-1.92 (m, 12H), 1.75-1.64 (m, 2H), 1.64-1.15 (m, 31H), 0.92-0.85 (m, 9H). Rf 0.45 (10% MeOH—CH2Cl2).

후처리

  1. temperatureThe solution was warmed to room temperature
  2. stirringstirred for 1 hour
  3. filtrationfiltered
  4. customto remove the ammonium salts and urea
  5. concentrationThe diethyl ether filtrate was concentrated in vacuo to dryness
  6. customThe residue was purified by column chromatography (100% ethyl acetate)

출처 및 근거

ORD 기록
ord-758afab1823f4443b99a1a546d9317cf
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09352042B2

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