4-Nitrobenzoyl chloride → Tert-butyl 3-(4-hydroxy-3-methoxyphenyl)-2-(4-nitrobenzamido)propanoate

HRID 1889159노트

반응식

HRID 1889159 반응식
[NH2:1][CH:2]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([O:18][CH3:19])[CH:12]=1)[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[N+:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1)([O-:22])=[O:21]>C(Cl)Cl>[OH:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH:2]([NH:1][C:27](=[O:28])[C:26]2[CH:25]=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[CH:31][CH:30]=2)[C:3]([O:5][C:6]([CH3:7])([CH3:9])[CH3:8])=[O:4])=[CH:12][C:13]=1[O:18][CH3:19]

참가 물질

4

반응물 2

HCID 85024-Nitrobenzoyl chlorideHCID 58545613Tert-butyl 2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoate

생성물 1

HCID 58545890Tert-butyl 3-(4-hydroxy-3-methoxyphenyl)-2-(4-nitrobenzamido)propanoate수율 44%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

Prepared using General Procedure 5: To a stirred solution of tert-butyl 2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoate INT-1 (1.85 g, 6.93 mmol) and TEA (1.93 mL, 13.9 mmol) in DCM (15 mL) at 0° C. was added 4-nitrobenzoyl chloride (1.29 g, 6.93 mmol) in DCM (10 mL) dropwise. The reaction mixture was stirred for 1 h, diluted with DCM (100 mL) and washed with saturated aqueous NaHCO3 (100 mL). The organic layer was dried over MgSO4, and concentrated. The product was purified by chromatography (EA/hexanes) to afford 1.38 g (44%) of tert-butyl 3-(4-hydroxy-3-methoxyphenyl)-2-(4-nitrobenzamido)propanoate INT-7. LCMS-ESI (m/z) calculated for C21H24N2O7: 416; found 415 [M−H]−, tR=2.18 min (Method 4).

후처리

  1. customPrepared
  2. washwashed with saturated aqueous NaHCO3 (100 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe product was purified by chromatography (EA/hexanes)

출처 및 근거

ORD 기록
ord-0b39fe5bcfd747f2bae90f9f0b72ec44
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501982B2

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