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

HRID 986360
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HRID 986360 반응식
[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]
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4b12e594976c4c188d2d04aad7c54a26
출처 데이터셋
uspto-grants-1987_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04711958

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