Acetic Acid → HCID 57419866, 화합물

HRID 1810458노트

반응식

HRID 1810458 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 57419866HCID 57419866, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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 (lint) 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.

후처리

  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

출처 및 근거

ORD 기록
ord-67e8cf584bb7425eafec5659e87e298a
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362044B2

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