Water → Propyl-carbamic acid (6R,7aS)-3-oxo-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-6-yl ester

HRID 455262ノート

反応式

HRID 455262 の反応式
[N:1]([CH2:4][CH2:5][CH3:6])=[C:2]=[O:3].[OH:7][C@H:8]1[CH2:27][N:11]2[C:12](=[O:26])[N:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[CH2:14][C@@H:10]2[CH2:9]1.O>C1COCC1.N1C=CC=CC=1>[O:26]=[C:12]1[N:11]2[CH2:27][C@H:8]([O:7][C:2](=[O:3])[NH:1][CH2:4][CH2:5][CH3:6])[CH2:9][C@H:10]2[CH2:14][N:13]1[C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:23])[F:24])=[CH:17][CH:16]=1

参加物

6

反応物 3

HCID 962WaterHCID 61033Propyl isocyanateHCID 70976331(6R,7aS)-6-Hydroxy-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one

生成物 1

HCID 71003226Propyl-carbamic acid (6R,7aS)-3-oxo-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-6-yl ester収率 26%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

1-Isocyanatopropane (30 mg, 0.4 mmol) was added to a solution of (6R,7aS)-6-Hydroxy-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (example 1, step e) (60 mg, 0.2 mmol) in anhydrous THF (10 mL) and pyridine (2 mL). The mixture was refluxed overnight. The mixture was cooled and poured into water (20 mL), extracted with ethyl acetate (3×20 mL). The organic layers was combined, washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=4:1) to give final compound 20 mg (26%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.60 (d, 2H, J=9.0 Hz), 7.19 (d, 2H, J=8.7 Hz), 5.35 (t, 1H, J=5.7), 4.71 (s, 1H), 4.17-4.00 (m, 3H), 3.74 (d, 1H, J=7.2 Hz), 3.22-3.12 (m, 3H), 2.23 (dd, 1H, J1=12.9 Hz, J2=3.3 Hz), 1.71-1.48 (m, 3H), 0.94 (t, 3H, J=7.2 Hz); LC-MS: 388.1 [M+1]+.

後処理

  1. temperatureThe mixture was refluxed overnight
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. washwashed with brine (20 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-8bcf50567cc4430babbfaae7de6fc56e
出典データセット
uspto-grants-2013_07
特許番号
US08497288B2

反応ノート

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