Tetrahydrofuran → (S)-3-(2-chloro-3-fluorobenzyl)-1-(1-hydroxypent-4-en-2-yl)-1-methylurea

HRID 340899노트

반응식

HRID 340899 반응식
C1C([N+]([O-])=O)=CC=C([Cl-][C:11]([O-:13])=O)C=1.Cl.[Cl:15][C:16]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][NH2:19].C[CH2:26][N:27](C(C)C)C(C)C.Cl.[CH3:35]N[C@@H](CC=C)CO.[CH2:43]1[CH2:47][O:46][CH2:45][CH2:44]1>>[Cl:15][C:16]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][NH:19][C:11](=[O:13])[N:27]([C@@H:43]([CH2:44][CH:45]=[CH2:35])[CH2:47][OH:46])[CH3:26]

참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran3회HCID 81531Diisopropylethylamine2회HCID 66622557(2-Chloro-3-fluorophenyl)methanamine hydrochlorideHCID 86635660(S)-2-(methylamino)pent-4-en-1-ol hydrochloride

생성물 1

HCID 57947623(S)-3-(2-chloro-3-fluorobenzyl)-1-(1-hydroxypent-4-en-2-yl)-1-methylurea수율 82%

실험 절차

To a solution of 4-nitrophenylchloroformate 8 (2.28 g, 11.3 mmol) in THF (10 mL) was added a solution of 2-chloro-3-fluorobenzylamine hydrochloride (2.22 g, 11.3 mmol) and DIEA (5.38 mL, 30.9 mmol) in THF (10 mL). The resulting solution was stirred at RT for 20 min. The reaction solution was added into a solution of (S)-2-(methylamino)pent-4-en-1-ol hydrochloride (10.3 mmol), DIEA (5.38 mL, 30.9 mmol) in THF (100 mL). The resulting solution was stirred at RT for 1 h. The solvent was removed, and the resulting residue was purified on silica gel column using a mixture of DCM and MeOH to give (S)-3-(2-chloro-3-fluorobenzyl)-1-(1-hydroxypent-4-en-2-yl)-1-methylurea (2.56 g, 82%) as a white solid. LRMS (M+H+) m/z 301.2.

후처리

  1. stirringThe resulting solution was stirred at RT for 1 h
  2. customThe solvent was removed
  3. customthe resulting residue was purified on silica gel column
  4. additiona mixture of DCM and MeOH

출처 및 근거

ORD 기록
ord-4691645a967d42bd880dbc1f328fe3bb
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895582B2

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