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Phenacyl bromide → L-isoleucine, N-[1-(2-phenyl-2-oxoethyl)-L-prolyl] benzylamide

HRID 2293347
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HRID 2293347 반응식
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[CH2:9]([NH:16][C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:32][C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34]>C(#N)C>[C:35]1([C:33](=[O:34])[CH2:32][N:1]2[CH2:8][CH2:7][CH2:6][C@H:2]2[C:3]([N:16]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])=[O:5])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1
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참가 물질

5

반응물 3

HCID 6259Phenacyl bromideHCID 10796Cesium carbonateHCID 86751513HCID 86751513, 화합물

생성물 1

HCID 67621189L-isoleucine, N-[1-(2-phenyl-2-oxoethyl)-L-prolyl] benzylamide수율 94%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Using the procedure described in example 5, treatment of L-proline-L-isoleucine benzylamide (361 mg, 1.14 mmol), with cesium carbonate (0.74 g, 2.28 mmol), and 2-bromoacetophenone (1.134 g, 5.69 mmol, 5.0 eq) in acetonitrile (12 mL), provided 466 mg (94%) of L-isoleucine, N-[1-(2-phenyl-2-oxoethyl)-L-prolyl] benzylamide as a pale yellow oil.

출처 및 근거

ORD 기록
ord-1807b6b7496a4fdf8004b42137c63c44
출처 데이터셋
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05686424

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