Diisopropylethylamine → HCID 67386290、化合物

HRID 1898504ノート

反応式

HRID 1898504 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 67386290HCID 67386290、化合物収率 68%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-51eb93e1791f447d9359d801e6fd4044
出典データセット
uspto-grants-2013_08
特許番号
US08518945B2

反応ノート

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