Diisopropylethylamine → HCID 67386290, 화합물

HRID 1898504노트

반응식

HRID 1898504 반응식
[C:1]([NH:8][C@@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.Cl.[C:37]([CH:39]1[CH2:42][NH:41][CH2:40]1)#[N:38].C(N(CC)C(C)C)(C)C>ClCCl.C(OCC)(=O)C.O>[C:4]([O:3][C:1](=[O:2])[NH:8][C@H:9]([CH3:10])[C:11]([N:41]1[CH2:42][CH:39]([C:37]#[N:38])[CH2:40]1)=[O:13])([CH3:5])([CH3:6])[CH3:7]

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 637606BOC-D-alanineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 45072465Azetidine-3-carbonitrile hydrochloride

생성물 1

HCID 67386290HCID 67386290, 화합물수율 68%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Boc-D-alanine (1.0 g, 5.29 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (1.87 g, 5.81 mmol) were dissolved in dichloromethane. 3-Cyanoazetidine hydrochloride (0.94 g, 7.93 mmol) and then N,N-diisopropylethylamine (2.3 mL, 13.2 mmol) were added and the mixture was stirred at room temperature for 16 h. Water and ethyl acetate were added and the layers were separated. The aqueous layer was extracted once more with ethyl acetate. The combined organic layers were washed with sodium chloride solution, dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography (ethyl acetate/hexanes) to provide 0.91 g (68%) of [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester.

후처리

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted once more with ethyl acetate
  3. washThe combined organic layers were washed with sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-51eb93e1791f447d9359d801e6fd4044
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518945B2

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