Benzyl Alcohol → HCID 178453647、化合物

HRID 1169409ノート

反応式

HRID 1169409 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13](C(O)=O)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C([N:38]([CH2:41]C)CC)C.[CH2:43]([OH:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C1(C)C=CC=CC=1.O>[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([NH:38][C:41](=[O:26])[O:50][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:14][CH2:15]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 178453624HCID 178453624、化合物

生成物 1

HCID 178453647HCID 178453647、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

A solution of trans-4-(tert-butoxycarbonylaminomethyl)cyclohexanecarboxylic acid (19.76 g), diphenylphosphoryl azide (25.36 g) and triethylamine (12 ml) in toluene (210 ml) was stirred at room temperature for 30 minutes and at 100° C. for 30 minutes. Into the reaction mixture was added benzyl alcohol (9.7 ml), and the resulting mixture was heated at reflux for 24 hours. After cooling to room temperature, the reaction mixture was mixed with water and was extracted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid, water, an aqueous saturated solution of sodium bicarbonate and an aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate. After the resulting organic layer was concentrated under reduced pressure, the residue was subjected to purification using column chromatography (ethyl acetate/hexane 1:2) and to recrystallization (ethyl acetate/hexane) to obtain benzyl trans-4-(tert-butoxycarbonylaminomethyl)cyclohexylcarbamate (18.93 g) as colorless crystals.

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 24 hours
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with 1 N hydrochloric acid, water
  5. dry with materialan aqueous saturated solution of sodium bicarbonate and an aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate
  6. concentrationAfter the resulting organic layer was concentrated under reduced pressure
  7. customthe residue was subjected to purification
  8. customto recrystallization (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-d5ecf802220349d4bb9db3f6d6338d7b
出典データセット
uspto-grants-2003_09
特許番号
US06627651B1

反応ノート

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