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Cyclohexylamine → (S)-Benzyl (1-(cyclohexylamino)-3-methyl-1-oxobutan-2-yl)carbamate

HRID 1032891
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HRID 1032891 반응식
[C:1]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH:34]1([NH2:40])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>C1COCC1.C(Cl)Cl.O>[CH:34]1([NH:40][C:16](=[O:18])[C@H:12]([CH:13]([CH3:14])[CH3:15])[NH:11][C:1]([O:3][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1
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참가 물질

8

반응물 4

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 726987N-Carbobenzoxy-L-valine

생성물 1

HCID 826228(S)-Benzyl (1-(cyclohexylamino)-3-methyl-1-oxobutan-2-yl)carbamate수율 87.2%

시약·촉매·용매 3

HCID 962Water
용매
HCID 6344Dichloromethane용매
HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A solution of carbobenzoxy-(S)-valine (1.26 g, 5 mmol) in anhydrous THF (20 ml) was vigorously stirred and thereto were added triethylamine (0.70 ml, 5 mmol) and isobutyl chloroformate (0.66 ml, 5 mmol) at 0° C. To this mixture was added cyclohexylamine (0.57 ml, 5 mmol) and this mixture was stirred for 2 hours at 0° C. and further for 24 hours at room temperature. The solvent was removed to obtain white crystals. These crystals were dissolved in a mixture of CH2Cl2 (80 ml) and water (30 ml). The organic layer was washed with 0.5M boric acid, a saturated aqueous sodium chloride solution, a saturated aqueous sodium hydrogencarbonate solution, a saturated aqueous sodium chloride solution and water (50 ml each) in succession, dried over Na2SO4 and concentrated under reduced pressure to obtain crude carbobenzoxy-(S)-valine cyclohexylamide (1.45 g, 87%), which was used as it was for the following reaction.

후처리

  1. customThe solvent was removed
  2. customto obtain white crystals
  3. washThe organic layer was washed with 0.5M boric acid
  4. dry with materiala saturated aqueous sodium chloride solution, a saturated aqueous sodium hydrogencarbonate solution, a saturated aqueous sodium chloride solution and water (50 ml each) in succession, dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-70ddc02ac51c4a66aff94eb7b92af1f5
출처 데이터셋
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05308820

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