tert-Butanol → Methyl 2-((tert-butoxycarbonyl)amino)-3-nitrobenzoate

HRID 397120

反応式

HRID 397120 の反応式
C([C:4]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.C([N:36]([CH2:39]C)CC)C.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>CN(C=O)C>[C:41]([O:45][C:39]([NH:36][C:4]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])=[O:24])([CH3:44])([CH3:43])[CH3:42]

参加物

6

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 43994772-(Methoxycarbonyl)-6-nitrobenzoic acid

生成物 1

HCID 9965968Methyl 2-((tert-butoxycarbonyl)amino)-3-nitrobenzoate収率 70%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of methyl 2-carboxy-3-nitrobenzoate (7.23 g) in DMF (50 ml) was added diphenylphosphoryl azide (11.3 g) at room temperature and then triethylamine (6.7 ml) was added dropwise to the stirred reaction mixture. After stirring at room temperature for 3 hours, tert-butanol (54 ml) was added to the stirred reaction mixture. After stirring at room temperature for 30 min., the reaction mixture was gradually warmed, then heated under reflux for 1 hour and evaporated to dryness. The resultant residue was dissolved in ethyl acetate, washed with dilute hydrochloric acid, aqueous sodium bicarbonate, and water, and then dried. After evaporation of the solvent, methanol was added to the resultant residue and the mixture was cooled to give colorless crystals (6.7 g, 70%).

後処理

  1. stirringAfter stirring at room temperature for 30 min.
  2. temperaturethe reaction mixture was gradually warmed
  3. temperatureheated
  4. temperatureunder reflux for 1 hour
  5. customevaporated to dryness
  6. dissolutionThe resultant residue was dissolved in ethyl acetate
  7. washwashed with dilute hydrochloric acid, aqueous sodium bicarbonate, and water
  8. customdried
  9. customAfter evaporation of the solvent, methanol
  10. additionwas added to the resultant residue
  11. temperaturethe mixture was cooled

出典と根拠

ORDレコード
ord-ee547fd9936a4114ac0b1c5cb01b93e1
出典データセット
uspto-grants-2003_08
特許番号
US06608210B2

関連ノート

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