Sodium Bicarbonate → tert-Butyl 2-methyl-2-[4-({[(4-methyl-1,3-oxazol-5-yl)methyl]amino}methyl)-phenoxy]-propanoate

HRID 1266527노트

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HRID 1266527 반응식
[CH:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]([CH3:17])([CH3:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:5][CH:4]=1)=O.[CH3:20][C:21]1[N:22]=[CH:23][O:24][C:25]=1[CH2:26][NH2:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[CH3:16][C:8]([O:7][C:6]1[CH:18]=[CH:19][C:3]([CH2:1][NH:27][CH2:26][C:25]2[O:24][CH:23]=[N:22][C:21]=2[CH3:20])=[CH:4][CH:5]=1)([CH3:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22708193tert-Butyl 2-(4-formylphenoxy)-2-methylpropanoateHCID 22708194(4-Methyl-1,3-oxazol-5-yl)methylamine

생성물 1

HCID 22708253tert-Butyl 2-methyl-2-[4-({[(4-methyl-1,3-oxazol-5-yl)methyl]amino}methyl)-phenoxy]-propanoate

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

1.25 g (4.73 mmol) of tert-butyl 2-(4-formylphenoxy)-2-methylpropanoate (Example I-4) and 0.64 g (5.67 mmol) of (4-methyl-1,3-oxazol-5-yl)methylamine (Example III-28) are together initially charged in 1,2-dichloroethane. At room temperature, 1.50 g (7.09 mmol) of sodium triacetoxyborohydride are added. The reaction mixture is stirred at room temperature for 4 hours and then admixed with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulphate and freed from the solvent under reduced pressure. The residue is purified chromatographically on silica gel (dichloromethane/methanol 30:1) and then dried under reduced pressure. This gives 1.104 g (65% of theory) of the title compound.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. customThe residue is purified chromatographically on silica gel (dichloromethane/methanol 30:1)
  4. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-336253dcd7664259adace0fb5fed48d3
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06548538B2

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