Benzyl 6-[(tert-butoxycarbonyl)amino]-5-oxo-4-(2,2,2-trifluoroethyl)-1,4-diazepane-1-carboxylate → tert-Butyl 7-oxo-1-(2,2,2-trifluoroethyl)-1,4-diazepan-6-ylcarbamate

HRID 20178

反応式

HRID 20178 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:15][N:14](C(OCC2C=CC=CC=2)=O)[CH2:13][CH2:12][N:11]([CH2:26][C:27]([F:30])([F:29])[F:28])[C:10]1=[O:31])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[O:31]=[C:10]1[N:11]([CH2:26][C:27]([F:28])([F:29])[F:30])[CH2:12][CH2:13][NH:14][CH2:15][CH:9]1[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4]

参加物

4

反応物 1

HCID 22293256Benzyl 6-[(tert-butoxycarbonyl)amino]-5-oxo-4-(2,2,2-trifluoroethyl)-1,4-diazepane-1-carboxylate

生成物 1

HCID 66939478tert-Butyl 7-oxo-1-(2,2,2-trifluoroethyl)-1,4-diazepan-6-ylcarbamate収率 102.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

10% Palladium on carbon (77 mg) was added to a solution of benzyl 6-[(tert-butoxycarbonyl)amino]-5-oxo-4-(2,2,2-trifluoroethyl)-1,4-diazepane-1-carboxylate (590 mg, 1.32 mmol) in ethanol (20 mL). The reaction vessel was evacuated and back-filled with nitrogen (3×), then back-filled with hydrogen (1 atm). After 18 h, the mixture was filtered and concentrated to give. the title compound (420 mg). MS 312 (M+1). 1H NMR (500 MHz, CDCl3) δ 5.83 (s, 1H), 4.53-4.49 (m, 1H), 4.29-4.20 (m, 1H), 3.96-3.88 (m, 1H), 3.81-3.77 (m, 1H), 3.38 (d, J=15.6 Hz, 1H), 3.26 (d, J=12.9 Hz, 1H), 3.16-3.13 (m, 1H), 2.81-2.79 (m, 1H), 2.72-2.67 (m, 1H), 1.83 (br s, 1H), 1.45 (s, 9H).

後処理

  1. customThe reaction vessel was evacuated
  2. additionback-filled with nitrogen (3×)
  3. additionback-filled with hydrogen (1 atm)
  4. filtrationthe mixture was filtered
  5. concentrationconcentrated
  6. customto give

出典と根拠

ORDレコード
ord-1d3c6cb8bf87430888ff109e9f80a32e
出典データセット
uspto-grants-2010_06
特許番号
US07745427B2

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