Thiourea → (S)-tert-butyl 2-(2-aminothiazol-4-yl)pyrrolidine-1-carboxylate

HRID 1685077ノート

反応式

HRID 1685077 の反応式
Cl[CH2:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=O.[NH2:17][C:18]([NH2:20])=[S:19]>C(O)C>[NH2:20][C:18]1[S:19][CH:2]=[C:3]([CH:5]2[CH2:9][CH2:8][CH2:7][N:6]2[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[N:17]=1

参加物

4

反応物 2

HCID 2723790ThioureaHCID 4072501Tert-butyl 2-(2-chloroacetyl)pyrrolidine-1-carboxylate

生成物 1

HCID 44118268(S)-tert-butyl 2-(2-aminothiazol-4-yl)pyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

An ethanol (20 mL) solution of tert-butyl 2-(2-chloroacetyl)pyrrolidine-1-carboxylate (1.08 g, 4.4 mol) and thiourea (334 mg, 4.4 mmol) was stirred at 55 C for 70 hours. Upon completion of the condensation, the solution was evaporated. The solid was dissolved in CH2Cl2 (100 mL). It was washed with dilute NaHCO3 solution, dried and evaporated. Recrystallization from CH2Cl2/hexane afforded tert-butyl 2-(2-aminothiazol-4-yl)pyrrolidine-1-carboxylate. 1H NMR (400 MHz, CDCl3): mixture of rotamers: δ 8.81 (s, 2H, br), 6.22 and 6.15 (2s, 1H), 4.84 and 4.78 (2s, 1H), 3.62 and 3.44 (2m, 2H), 2.4-1.8 (m, 4H), 1.46 and 1.36 (2s, 9H). MS (ES+): M/Z 270 (M+H)+, 170 (M−C5H8O2)+.

後処理

  1. customUpon completion of the condensation
  2. customthe solution was evaporated
  3. dissolutionThe solid was dissolved in CH2Cl2 (100 mL)
  4. washIt was washed with dilute NaHCO3 solution
  5. customdried
  6. customevaporated
  7. customRecrystallization from CH2Cl2/hexane

出典と根拠

ORDレコード
ord-0ea6ae08f8b14dd9bc7670566ca6aff0
出典データセット
uspto-grants-2012_04
特許番号
US08148380B2

反応ノート

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