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

HRID 2410644ノート

反応式

HRID 2410644 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-76b7b6d9fe2b4e3294824abf91ab5c78
出典データセット
uspto-grants-2014_08
特許番号
US08816121B2

反応ノート

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