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

HRID 216060
ノート
印刷プレビュー

反応式

HRID 216060 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:17][O:18][CH3:19])([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.[CH3:32][N:33]([CH3:44])[C:34](=[O:43])[O:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([NH2:42])[CH:37]=1>CN(C=O)C.C(Cl)Cl.C(OCC)(=O)C>[CH3:32][N:33]([CH3:44])[C:34]([O:35][C:36]1[CH:37]=[C:38]([NH:42][C:14]([C:11]2([CH2:17][O:18][CH3:19])[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:39]=[CH:40][CH:41]=1)=[O:43]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 1049PyridineHCID 298773-Aminophenyl dimethylcarbamateHCID 65578Oxalyl chlorideHCID 218825761-((Tert-butoxy)carbonyl)-4-(methoxymethyl)piperidine-4-carboxylic acid

生成物 1

HCID 67037885Tert-butyl 4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)-4-(methoxymethyl)piperidine-1-carboxylate収率 90%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒
HCID 6344Dichloromethane溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 1-(tert-butoxycarbonyl)-4-(methoxymethyl)-piperidine-4-carboxylic acid from step B (718 mg, 2.63 mmol), pyridine (0.84 mL, 10.52 mmol), and DMF (catalytic, 3 drops) in CH2Cl2 (13 mL) was added dropwise oxalyl chloride (0.25 mL, 2.89 mmol, caution: exothermic). After gas evolution subsided, the reaction was stirred at ambient temperature for 30 minutes. 3-Aminophenyl dimethylcarbamate (475 mg, 2.63 mmol) was added in one portion to this solution and stirred for another 30 minutes. The reaction was quenched with saturated aqueous NH4Cl, and the aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. Silica gel chromatography (50% ethyl acetate:hexanes) afforded the title compound (1.03 g, 90% yield for two steps). MS (ES+) [M+NH4]+=453.3

後処理

  1. stirringstirred for another 30 minutes
  2. customThe reaction was quenched with saturated aqueous 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 over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-5c25f9b1b6944ba69aa640a29dd05064
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08193202B2

反応ノート

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