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

HRID 416328ノート

反応式

HRID 416328 の反応式
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]

参加物

5

反応物 4

HCID 8028Tetrahydrofuran3 回HCID 81531Diisopropylethylamine2 回HCID 66622557(2-Chloro-3-fluorophenyl)methanamine hydrochlorideHCID 86635660(S)-2-(methylamino)pent-4-en-1-ol hydrochloride

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-66553a29caf64e49a56140e3121d7e36
出典データセット
uspto-grants-2012_01
特許番号
US08088793B2

反応ノート

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