3-Fluorobenzylamine → Tert-butyl 2-(4-(3-fluoro-2-methylbenzylcarbamoyl)-4-(hydroxymethyl)piperidin-1-yl)-2-oxoethylcarbamate

HRID 655970노트

반응식

HRID 655970 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([N:12]1[CH2:17][CH2:16][C:15]([CH2:21][OH:22])([C:18]([OH:20])=O)[CH2:14][CH2:13]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:47][C:48]1[CH:49]=[C:50]([CH:53]=[CH:54][CH:55]=1)[CH2:51][NH2:52].CCN(C(C)C)C(C)C>CN(C=O)C>[F:47][C:48]1[C:49]([CH3:23])=[C:50]([CH:53]=[CH:54][CH:55]=1)[CH2:51][NH:52][C:18]([C:15]1([CH2:21][OH:22])[CH2:14][CH2:13][N:12]([C:10](=[O:11])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2])[CH2:17][CH2:16]1)=[O:20]

참가 물질

6

반응물 4

HCID 668533-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579202801-(2-(Tert-butoxycarbonylamino)acetyl)-4-(hydroxymethyl)piperidine-4-carboxylic acid

생성물 1

HCID 59778520Tert-butyl 2-(4-(3-fluoro-2-methylbenzylcarbamoyl)-4-(hydroxymethyl)piperidin-1-yl)-2-oxoethylcarbamate수율 111.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of crude 1-(2-(tert-butoxycarbonylamino)acetyl)-4-(hydroxymethyl)piperidine-4-carboxylic acid (120 mg, ˜0.379 mmol, 1.0 equiv) in DMF (30 mL) were added HBTU (144 mg, 0.379 mmol, 1.0 equiv.), 2-methyl, 3-fluorobenzylamine (53 mg, 0.379 mmol, 1.0 equiv.) and DIEA (132 μL, 0.758 mmol, 2.0 equiv.). The reaction mixture was stirred overnight at rt. The mixture was partitioned between EtOAc and H2O. The organic layer was washed by 1 N HCl, Saturated NaHCO3, water and brine, dried over Na2SO4, and concentrated to dryness to give tert-butyl 2-(4-(3-fluoro-2-methylbenzylcarbamoyl)-4-(hydroxymethyl)piperidin-1-yl)-2-oxoethylcarbamate (185 mg), which was used without further purification. LRMS (M+H+) m/z 439.1.

후처리

  1. customThe mixture was partitioned between EtOAc and H2O
  2. washThe organic layer was washed by 1 N HCl, Saturated NaHCO3, water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-987870ed313d4dc68a56f55ea39004ef
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071625B2

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