Pyridine → Tert-butyl 4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)-4-(2-methoxyethoxy)piperidine-1-carboxylate

HRID 216087ノート

反応式

HRID 216087 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([O:17][CH2:18][CH2:19][O:20][CH3:21])([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.[CH3:34][N:35]([CH3:46])[C:36](=[O:45])[O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([NH2:44])[CH:39]=1>CN(C=O)C.C(Cl)Cl>[CH3:34][N:35]([CH3:46])[C:36]([O:37][C:38]1[CH:39]=[C:40]([NH:44][C:14]([C:11]2([O:17][CH2:18][CH2:19][O:20][CH3:21])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)=[O:16])[CH:41]=[CH:42][CH:43]=1)=[O:45]

参加物

7

反応物 4

HCID 1049PyridineHCID 298773-Aminophenyl dimethylcarbamateHCID 65578Oxalyl chlorideHCID 670367781-(Tert-butoxycarbonyl)-4-(2-methoxyethoxy)piperidine-4-carboxylic acid

生成物 1

HCID 67036832Tert-butyl 4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)-4-(2-methoxyethoxy)piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of carboxylic acids from step B, pyridine (0.2 mL, 2.48 mmol), and DMF (catalytic, 2 drops) in CH2Cl2 (3.1 mL) was added dropwise oxalyl chloride (60 μL, 0.68 mmol, caution: exothermic). After gas evolution subsided, the reaction was stirred at ambient temperature for 30 minutes. 3-Aminophenyl dimethylcarbamate (112 mg, 0.62 mmol) was added in one portion to this solution, which was stirred for another 30 minutes. The reaction was quenched with saturated aq. NH4Cl, and the aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried with MgSO4, filtered, and concentrated under vacuum. Silica gel chromatography (80% ethyl acetate:hexanes) afforded the title compound as an off-white solid (150 mg). MS (ES+) [M+CH3CN]+=529.3.

後処理

  1. stirringwas stirred for another 30 minutes
  2. customThe reaction was quenched with saturated aq. NH4Cl
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-be8ed48330cb40a5986e3afa4b1b6d46
出典データセット
uspto-grants-2012_06
特許番号
US08193202B2

反応ノート

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