Acetic Acid → HCID 71060280、化合物

HRID 1036716ノート

反応式

HRID 1036716 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:21](=[O:23])[NH2:22])([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:24](OCC)(OCC)OCC.C(O)(=O)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]2([N:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:24]=[N:22][C:21]2=[O:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 31214Ethyl orthoformateHCID 710601663-Carbamoyl-3-phenylamino-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 71060280HCID 71060280、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 3-carbamoyl-3-phenylamino-piperidine-1-carboxylic acid tert-butyl ester (300 mg, 0.94 mmol) in toluene (10 ml) was added triethyl orthoformate (0.47 ml, 2.8 mmol) and acetic acid (0.5 ml, 8.7 mmol). The mixture was heated at reflux overnight. The reaction mixture was cooled and washed with a saturated solution of sodium bicarbonate (25 ml). The organics were separated and the aqueous extracted with EtOAc (10 ml). The organics portions were combined, dried (MgSO4) and concentrated in vacuo to afford an oil. Purification of the crude product by chromatography on silica eluting with 0-50% EtOAc in iso-hexane afforded the title compound.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture was cooled
  4. washwashed with a saturated solution of sodium bicarbonate (25 ml)
  5. customThe organics were separated
  6. extractionthe aqueous extracted with EtOAc (10 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto afford an oil
  10. customPurification of the crude product by chromatography on silica eluting with 0-50% EtOAc in iso-hexane

出典と根拠

ORDレコード
ord-8a2f1589726f4deb9ad1e57781d3c575
出典データセット
uspto-grants-2013_10
特許番号
US08546416B2

反応ノート

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