Acetic Acid → HCID 68772648, 화합물

HRID 1398926노트

반응식

HRID 1398926 반응식
[NH2:1][C:2]1[C:7]2[N:8]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:9]([CH:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[OH:12])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:27](O)(=O)[CH3:28].[CH:31](=O)[CH3:32].C(O[BH3-])(=O)C.[Na+]>CO>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[CH:11]([OH:12])[C:9]1[N:8]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:7]2[C:2]([N:1]([CH2:27][CH3:28])[CH2:31][CH3:32])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 23670382SodiumacetoxyborohydrideHCID 68773584HCID 68773584, 화합물

생성물 1

HCID 68772648HCID 68772648, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a suspension of methyl 3-{7-amino-2-[(2,4-dichlorophenyl)(hydroxy)methyl]-1H-benzimidazol-1-yl}propanoate (6.00 g, 14.7 mmol) and acetic acid (7.4 mL) in methanol (147 mL) was added acetaldehyde (4.95 mL, 88.2 mmol) at 0° C. After 30 min, sodium acetoxyborohydride (18.7 g, 88.2 mmol) was added. After 2 h, the reaction mixture was quenched with water, concentrated in vacuo, diluted with ethyl acetate, washed with aqueous sodium hydroxide (1 M) and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless amorphous (6.30 g, 13.6 mmol, 92%).

후처리

  1. waitAfter 2 h
  2. customthe reaction mixture was quenched with water
  3. concentrationconcentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washwashed with aqueous sodium hydroxide (1 M) and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture

출처 및 근거

ORD 기록
ord-a6ee35376a1343e29923510a63ddcdb1
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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