Isophthalaldehyde → Di-tert-butyl (((((1,3-phenylenebis(methylene))bis(azanediyl))bis(propane-3,1-diyl))bis(azanediyl))bis(propane-3,1-diyl))dicarbamate

HRID 58966

반응식

HRID 58966 반응식
[CH:1](=O)[C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=O)[CH:3]=1.[NH2:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].[BH4-].[Na+]>CO>[C:4]1([CH2:5][NH:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH:7]=[CH:8][CH:9]=[C:2]([CH2:1][NH:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[CH:3]=1

참가 물질

5

반응물 3

HCID 34777IsophthalaldehydeHCID 27866321,1-Dimethylethyl N-(3-((3-aminopropyl)amino)propyl)carbamateHCID 4311764Sodium borohydride

생성물 1

HCID 117633421Di-tert-butyl (((((1,3-phenylenebis(methylene))bis(azanediyl))bis(propane-3,1-diyl))bis(azanediyl))bis(propane-3,1-diyl))dicarbamate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Isophthalaldehyde (1.07 g, 7.99 mmol) and MeOH (50 mL) were added to a round-bottom flask. To the solution was added tert-butyl (3-((3-aminopropyl)amino)propyl)carbamate (3.69 g, 16.0 mmol) and the reaction mixture was stirred for 24 h. Sodium borohydride (1.21 g, 32.0 mmol) was added portionwise and stirred for 1 h. The reaction mixture was concentrated under reduced pressure, and aq. NaOH (10%, 150 mL) and EtOAc (150 mL) were added. The layers were separated, and the aqueous layer was extracted with EtOAc (150 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the desired product as a clear oil. The intermediate was carried forward without further purification.

후처리

  1. stirringstirred for 1 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and aq. NaOH (10%, 150 mL) and EtOAc (150 mL)
  3. additionwere added
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (150 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c68bf2c627ce430aa507bc115a2b1ecb
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09439433B2

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