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

HRID 1685077노트

반응식

HRID 1685077 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-0ea6ae08f8b14dd9bc7670566ca6aff0
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148380B2

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