3-Hydroxybenzaldehyde → Methyl 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)acrylate

HRID 449503

반응식

HRID 449503 반응식
[C:1]([O:5][C:6]([NH:8][CH:9](P(OC)(OC)=O)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=O.C1CCN2C(=NCCC2)CC1>C(Cl)Cl.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C:9](=[CH:24][C:23]1[CH:26]=[CH:27][CH:28]=[C:21]([OH:20])[CH:22]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 3

HCID 1013-HydroxybenzaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 397380Methyl ((tert-butoxy(hydroxy)methylidene)amino)(dimethoxyphosphoryl)acetate

생성물 1

HCID 67542936Methyl 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)acrylate수율 96%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Methyl [(tert-butoxycarbonyl)amino](dimethoxyphosphoryl)acetate (Fluka, Cat. #09659) (0.97 g, 3.3 mmol) and 3-hydroxybenzaldehyde (0.400 g, 3.28 mmol) were combined in methylene chloride (14 mL) at r.t. under nitrogen. To this DBU (0.68 mL, 3.9 mmol) was added and the reaction was stirred at r.t. for 2 h. The reaction was taken up in ethyl acetate, washed with 1 N HCl, brine, dried over magnesium sulfate and concentrated under reduced pressure to give the crude product as an oil. The product was purified by Flash chromatography on a silica gel column eluting hexane: ethyl acetate gradient to give methyl 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)acrylate (0.92 g, 96%) as a clear oil Analytical LCMS (M+H-Boc)+: m/z=193.9.

후처리

  1. washwashed with 1 N HCl, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give the crude product as an oil
  5. customThe product was purified by Flash chromatography on a silica gel column
  6. washeluting hexane

출처 및 근거

ORD 기록
ord-c0676be429e740f2b8ede788a3d1cdd5
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481732B2

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