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Dicyclohexylcarbodiimide → (2RS, 3S)-3-(tert-butoxycarbonyl)amino-4-cyclohexyl-2-hydroxy-N-isobutylbutyramide

HRID 986360
ノート
印刷プレビュー

反応式

HRID 986360 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH:10]([OH:14])[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:23]([NH2:27])[CH:24]([CH3:26])[CH3:25].OS1C2C=CC=CC=2N=C1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH:10]([OH:14])[C:11]([NH:27][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 12206183Isobutylamine HydrochlorideHCID 59490980(2RS, 3S)-3-tert-butoxycarbonylamino-4-cyclohexyl-2-hydroxybutyric acidHCID 178527226HCID 178527226、化合物

生成物 1

HCID 86741924(2RS, 3S)-3-(tert-butoxycarbonyl)amino-4-cyclohexyl-2-hydroxy-N-isobutylbutyramide収率 125.8%

試薬・触媒・溶媒 2

HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 400 mg of the butyric acid compound, 175 mg of isobutylamine hydrochloride, 270 mg of 1-hydroxybenzotiazole and 0.22 ml of triethylamine in 20 ml of ethyl acetate was added 300 mg of dicyclohexylcarbodiimide with stirring under ice-cooling, and then the mixture was still stirred for 16 hours. The reaction mixture was cooled, and filtered to remove insoluble materials. The filtrate was washed successively with an aqueous citric acid solution, a 5% aqueous sodium bicarbonate solution and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to obtain 595 mg of (2RS, 3S)-3-(tert-butoxycarbonyl)amino-4-cyclohexyl-2-hydroxy-N-isobutylbutyramide.

後処理

  1. temperaturecooling
  2. stirringthe mixture was still stirred for 16 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customto remove insoluble materials
  6. washThe filtrate was washed successively with an aqueous citric acid solution
  7. dry with materiala 5% aqueous sodium bicarbonate solution and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-4b12e594976c4c188d2d04aad7c54a26
出典データセット
uspto-grants-1987_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04711958

反応ノート

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