Diisopropylethylamine → (S)-1-(1,1-Dioxo-1lambda6-thiomorpholine-4-carbonyl)-perhydro-azepine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

HRID 336217노트

반응식

HRID 336217 반응식
Cl.[C:2]([C:6]1[O:10][N:9]=[C:8]([NH:11][C:12]([C@@H:14]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][NH:15]2)=[O:13])[CH:7]=1)([CH3:5])([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.[O:30]=[S:31]1(=[O:40])[CH2:36][CH2:35][N:34]([C:37](Cl)=[O:38])[CH2:33][CH2:32]1>CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:2]([C:6]1[O:10][N:9]=[C:8]([NH:11][C:12]([C@@H:14]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]2[C:37]([N:34]2[CH2:35][CH2:36][S:31](=[O:40])(=[O:30])[CH2:32][CH2:33]2)=[O:38])=[O:13])[CH:7]=1)([CH3:5])([CH3:3])[CH3:4]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 216949071,1-Dioxo-1lambda6-thiomorpholine-4-carbonyl chlorideHCID 86660403(S)-Perhydro-azepine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide hydrochloride

생성물 1

HCID 58564080(S)-1-(1,1-Dioxo-1lambda6-thiomorpholine-4-carbonyl)-perhydro-azepine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8857Ethyl Acetate용매

실험 절차

A solution of (S)-perhydro-azepine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide hydrochloride (0.30 g, 1.13 mmol), DIPEA (0.32 g, 2.48 mmol) and DMAP (16.0 mg, 0.13 mmol) is stirred at room temperature for 15 minutes. 1,1-Dioxo-1λ6-thiomorpholine-4-carbonyl chloride (0.27 g, 1.35 mmol) (prepared according to method M step 1) is added drop wise at 0° C. to the reaction mixture that is slowly warmed up to room temperature and stirred for 14 hours. The reaction mixture is diluted with EtOAc, washed with water and brine. After drying the organic phase over anhydrous Na2SO4, removal of the solvent under reduced pressured affords the crude product that is purified by prep TLC to afford the title product; m/z 427 [M+H+].

후처리

  1. washwashed with water and brine
  2. customAfter drying the organic phase
  3. customover anhydrous Na2SO4, removal of the solvent
  4. customaffords the crude product that
  5. customis purified by prep TLC

출처 및 근거

ORD 기록
ord-70be7240cd7341b8bc9b56d410acef49
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889670B2

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