Chloroacetaldehyde → HCID 57906525, 화합물

HRID 420489노트

반응식

HRID 420489 반응식
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[C:14]([Br:15])=[CH:13][N:12]=[C:11]([NH2:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].Cl[CH2:24][CH:25]=O>>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[C:14]([Br:15])=[CH:13][N:12]2[CH:24]=[CH:25][N:16]=[C:11]2[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 57906440HCID 57906440, 화합물

생성물 1

HCID 57906525HCID 57906525, 화합물수율 79%

실험 절차

A mixture of (2-amino-5-bromo-pyridin-4-ylmethyl)-carbamic acid tert-butyl ester (1.0 g, 3.3 mmol), NaHCO3 (474 mg, 5.6 mmol) and chloracetaldehyde (2.2 mL, 15.0 mmol) was vigorously stirred and refluxed for 14 h. The reaction mixture was cooled to RT, concentrated under vacuum and the remaining residue was suspended in DCM and brine. The aqueous layer was separated and extracted with DCM (5×), and the combined organic fractions were dried over Na2SO4, filtered, and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, hexane/DCM/TBME 10:10:1→1:1:18) to yield the title compound (860 mg, 2.6 mmol, 79%) as a pale yellow solid. MS: 327 [M+1]+; HPLC: AtRet=1.07; TLC: RF 0.16 (hexane/DCM/TBME 1:1:2).

후처리

  1. temperaturerefluxed for 14 h
  2. concentrationconcentrated under vacuum
  3. customThe aqueous layer was separated
  4. extractionextracted with DCM (5×)
  5. dry with materialthe combined organic fractions were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, hexane/DCM/TBME 10:10:1→1:1:18)

출처 및 근거

ORD 기록
ord-62a3cb6af6e6429f8177b787841b741e
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097617B2

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