Sodium cyanoborohydride → (S)-1-(Tetrahydro-pyran-4-ylmethyl)-azepane-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

HRID 336218노트

반응식

HRID 336218 반응식
C([BH3-])#N.[Na+].[O:5]1[CH2:10][CH2:9][CH:8]([CH:11]=O)[CH2:7][CH2:6]1.Cl.[C:14]([C:18]1[O:22][N:21]=[C:20]([NH:23][C:24]([C@@H:26]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][NH:27]2)=[O:25])[CH:19]=1)([CH3:17])([CH3:16])[CH3:15]>CN(C=O)C.CCOC(C)=O>[C:14]([C:18]1[O:22][N:21]=[C:20]([NH:23][C:24]([C@@H:26]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][N:27]2[CH2:11][CH:8]2[CH2:7][CH2:6][O:5][CH2:10][CH2:9]2)=[O:25])[CH:19]=1)([CH3:17])([CH3:15])[CH3:16]

참가 물질

6

반응물 3

HCID 5003444Sodium cyanoborohydrideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 86660403(S)-Perhydro-azepine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide hydrochloride

생성물 1

HCID 58563913(S)-1-(Tetrahydro-pyran-4-ylmethyl)-azepane-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Sodium cyanoborohydride (0.19 g, 3.02 mmol) and tetrahydro-pyran-4-carbaldehyde (0.26 g, 2.26 mmol) is added to a solution of (S)-perhydro-azepine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide hydrochloride (prepared according to Method T, step 6) (0.4 g, 1.51 mmol) in DMF (5.0 mL). After stirring for four hours, the reaction mixture is diluted with EtOAc and washed twice with water. The organic phase is dried over anhydrous Na2SO4 and after removal of the solvent under reduced pressure, the crude is purified by prep TLC to afford the title compound; m/z 364 [M+H].

후처리

  1. washwashed twice with water
  2. dry with materialThe organic phase is dried over anhydrous Na2SO4
  3. customafter removal of the solvent under reduced pressure
  4. customthe crude is purified by prep TLC

출처 및 근거

ORD 기록
ord-e9cb4a17530d4635900ad0729b303dbb
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889670B2

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