Acetic Acid → HCID 57419866、化合物

HRID 1920017ノート

反応式

HRID 1920017 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.[CH2:14]([NH2:16])[CH3:15].C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:14]([NH:16][CH2:4][C:3]1[CH:6]=[C:7]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:8]=[CH:9][C:2]=1[OH:1])[CH3:15]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 5003444Sodium cyanoborohydrideHCID 574198652-Hydroxy-5-(methanesulfonyl)benzaldehyde

生成物 1

HCID 57419866HCID 57419866、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

2-Hydroxy-5-methanesulfonyl-benzaldehyde (0.200 g, 1.0 mmol), ethylamine (2M in THF; 0.75 mL, 1.5 mmol), and sodium cyanoborohydride (0.095 g, 1.5 mmol) were combined in MeOH (10 mL). 4 Å Molecular sieves were added, followed by acetic acid (0.09 mL, 1.5 mmol), and the reaction was stirred for 1 hour. The mixture was filtered, and H2O (0.5 mL) was added and the solution was concentrated. The residue was partitioned between EtOAc (100 mL) and brine (20 mL), and the mixture was neutralized with 1N aqueous HCl (1 mL) and extracted six times with EtOAc, until minimal product was seen in the aqueous layer by analytical tlc. The combined organic layers were dried, filtered, and concentrated to give the title compound.

後処理

  1. addition4 Å Molecular sieves were added
  2. filtrationThe mixture was filtered
  3. additionH2O (0.5 mL) was added
  4. concentrationthe solution was concentrated
  5. customThe residue was partitioned between EtOAc (100 mL) and brine (20 mL)
  6. extractionextracted six times with EtOAc
  7. customThe combined organic layers were dried
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-55c186d2b6f2417286521f8e670d0864
出典データセット
uspto-grants-2012_05
特許番号
US08168678B2

反応ノート

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