Chloroacetaldehyde → HCID 57906525、化合物

HRID 420489ノート

反応式

HRID 420489 の反応式
[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]

参加物

4

反応物 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 57906440HCID 57906440、化合物

生成物 1

HCID 57906525HCID 57906525、化合物収率 79%

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-62a3cb6af6e6429f8177b787841b741e
出典データセット
uspto-grants-2012_01
特許番号
US08097617B2

反応ノート

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