Sodium hydride → Benzyl 6-[(tert-butoxycarbonyl)amino]-5-oxo-4-(2,2,2-trifluoroethyl)-1,4-diazepane-1-carboxylate

HRID 493688

反応式

HRID 493688 の反応式
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][CH:11]1[CH2:17][N:16]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:15][CH2:14][NH:13][C:12]1=[O:28])=[O:9])([CH3:6])([CH3:5])[CH3:4].ClC(Cl)(Cl)S(O[CH2:35][C:36]([F:39])([F:38])[F:37])(=O)=O.ClC(Cl)(Cl)S([O-])(=O)=O>CN(C)C=O>[C:3]([O:7][C:8]([NH:10][CH:11]1[CH2:17][N:16]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:15][CH2:14][N:13]([CH2:35][C:36]([F:39])([F:38])[F:37])[C:12]1=[O:28])=[O:9])([CH3:6])([CH3:4])[CH3:5]

参加物

6

反応物 4

HCID 24758Sodium hydride2 回HCID 900272,2,2-Trifluoroethyl trichloromethanesulphonateHCID 22293222TrichloromethanesulfonateHCID 22293224Benzyl 6-[(tert-butoxycarbonyl)amino]-5-oxo-1,4-diazepane-1-carboxylate

生成物 1

HCID 22293256Benzyl 6-[(tert-butoxycarbonyl)amino]-5-oxo-4-(2,2,2-trifluoroethyl)-1,4-diazepane-1-carboxylate収率 42%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
-35 °C

実験手順

Sodium hydride (60% dispersion in mineral oil; 180 mg, 4.43 mmol) was added to a solution of benzyl 6-[(tert-butoxycarbonyl)amino]-5-oxo-1,4-diazepane-1-carboxylate (1.34 g, 3.69 mmol) in N,N-dimethylformamide (25 mL) at −35° C. After 15 min, 2,2,2-trifluoroethyl trichloromethanesulfonate (0.911 mL, 5.54 mmol) was added and the reaction was stirred at −35° C. After 2 h, an additional amount of sodium hydride (100 mg, 2.5 mmol) and trichloromethanesulfonate (0.500 mL, 3.04 mmol) were added. After 18 h, the reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was washed with water (3×), saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (hexanes→30% ethyl acetate/hexanes) gave the title compound (690 mg). MS 446 (M+1).

後処理

  1. waitAfter 2 h
  2. waitAfter 18 h
  3. customthe reaction was quenched with water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water (3×), saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography (hexanes→30% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-ad72f65d0021466181a25828bd23972e
出典データセット
uspto-grants-2009_05
特許番号
US07534784B2

関連ノート

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