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

HRID 409823ノート

反応式

HRID 409823 の反応式
[Si]([O:8][CH2:9][C@@H:10]([N:14]([CH3:27])[C:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[Cl:26])=[O:16])[CH2:11][CH:12]=[CH2:13])(C(C)(C)C)(C)C.Cl>CO>[Cl:26][C:20]1[C:21]([F:25])=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][NH:17][C:15](=[O:16])[N:14]([C@@H:10]([CH2:11][CH:12]=[CH2:13])[CH2:9][OH:8])[CH3:27]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 57947454(S)-1-(1-(tert-butyldimethylsilyloxy)pent-4-en-2-yl)-3-(2-chloro-3-fluorobenzyl)-1-methylurea

生成物 1

HCID 57947623(S)-3-(2-chloro-3-fluorobenzyl)-1-(1-hydroxypent-4-en-2-yl)-1-methylurea収率 77%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of (S)-1-(1-(tert-butyldimethylsilyloxy)pent-4-en-2-yl)-3-(2-chloro-3-fluorobenzyl)-1-methylurea (5.80 g, 10.8 mmol) in MeOH (50 mL) was added HCl (1N, 32.0 mL). The resulting solution was stirred at RT for 30 min. The mixture was partially concentrated and filtered. The filtrate was purified on RP-HPLC using a mixture of acetonitrile and water to give (S)-3-(2-chloro-3-fluorobenzyl)-1-(1-hydroxypent-4-en-2-yl)-1-methylurea (2.0 g, 77%) as a white solid, which was used without further purification. LRMS (M+H+) m/z 301.2.

後処理

  1. concentrationThe mixture was partially concentrated
  2. filtrationfiltered
  3. customThe filtrate was purified on RP-HPLC
  4. additiona mixture of acetonitrile and water

出典と根拠

ORDレコード
ord-a56495bffc3b465e88a134d4d492591d
出典データセット
uspto-grants-2014_06
特許番号
US08759374B2

反応ノート

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