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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-Butyl [(1R)-1-{[(cyclohexylmethyl)amino]carbonyl)-3-(methylthio)propyl]carbamate

HRID 226458
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HRID 226458 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][CH2:14][S:15][CH3:16])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:17]1([CH2:23][NH2:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(C)=O.O>[CH:17]1([CH2:23][NH:24][C:10]([C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][CH2:14][S:15][CH3:16])=[O:12])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1
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참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 76688CyclohexanemethylamineHCID 111051N-(tert-Butyloxycarbonyl)-D-methionine

생성물 1

HCID 86603753tert-Butyl [(1R)-1-{[(cyclohexylmethyl)amino]carbonyl)-3-(methylthio)propyl]carbamate수율 89.5%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 22728543Water ethylacetate용매

실험 절차

A mixture of (2R)-2-[(tert-butoxycarbonyl)amino]-4-(methylthio)butanoic acid (4.57 g), cyclohexanemethylamine (2.28 g), HOBt (2.72 g), and EDCI (3.87 g) in DMF (50 mL) was stirred at ambient temperature for 15 hours. The reaction mixture was poured into a mixture of AcOEt-H2O and the organic layer was washed with aqueous ammonium chloride, aqueous sodium hydrogen carbonate, and brine and dried over MgSO4. The solvent was evaporated in vacuo and the residue was crystallized from ethyl acetate and hexane to give tert-butyl [(1R)-1-{[(cyclohexylmethyl)amino]carbonyl}-3-(methylthio)propyl]carbamate (5.65 g).

후처리

  1. washthe organic layer was washed with aqueous ammonium chloride, aqueous sodium hydrogen carbonate, and brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was crystallized from ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-d8e0caea98d8486b94d4cb0ed2320a49
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07557127B2

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