Sodium Hydroxide → HCID 18387433, 화합물

HRID 2296760노트

반응식

HRID 2296760 반응식
[NH2:1][CH2:2][CH2:3][C:4]1[S:5][C:6]2[CH:32]=[CH:31][CH:30]=[CH:29][C:7]=2[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])=[CH:15][CH:14]=2)[C:9](=[O:11])[CH:10]=1.[CH3:33][O:34][C:35]1[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:36]=1[CH:37]=O.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH3:33][O:34][C:35]1[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:36]=1[CH2:37][NH:1][CH2:2][CH2:3][C:4]1[S:5][C:6]2[CH:32]=[CH:31][CH:30]=[CH:29][C:7]=2[N:8]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:28])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])=[CH:17][CH:18]=2)[C:9](=[O:11])[CH:10]=1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 691752,4-DimethoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 18387460HCID 18387460, 화합물

생성물 1

HCID 18387433HCID 18387433, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

A mixture of Compound 7 as prepared in Example 31 (0.105 g, 0.24 mM), 2,4-dimethoxybenzaldehyde (0.040 g, 0.240 mM) and acetic acid (0.05 ml) in methanol was stirred at room temperature for three hours and 2.5 equivalence of sodium cyanoborohydride was added. The mixture was stirred at room temperature for an additional 4 hours and a 6N NaOH (0.5 ml; adjusted to pH8) was added. The methanol was removed under reduced pressure and the residue diluted with water (50 ml) and extracted with ethyl acetate (2×5 ml). The ethyl acetate extracts were dried (MgSO4), evaporated in vacuo and purified by flash column chromatography (EM silica gel 60; 5% MeOH in CH2Cl2) to give a white solid product. m/z (MH+) 596.

후처리

  1. stirringThe mixture was stirred at room temperature for an additional 4 hours
  2. customThe methanol was removed under reduced pressure
  3. additionthe residue diluted with water (50 ml)
  4. extractionextracted with ethyl acetate (2×5 ml)
  5. dry with materialThe ethyl acetate extracts were dried (MgSO4)
  6. customevaporated in vacuo
  7. custompurified by flash column chromatography (EM silica gel 60; 5% MeOH in CH2Cl2)
  8. customto give a white solid product

출처 및 근거

ORD 기록
ord-6e572664b85d464ea3e3c0c265f84a7b
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06489321B1

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