Water → tert-Butyl 7-chloro-2-oxo-1,2,3,5-tetrahydro-4H-1,4-benzodiazepine-4-carboxylate

HRID 237334ノート

反応式

HRID 237334 の反応式
C([O:3][C:4](=O)[CH2:5][N:6]([CH2:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[NH2:22])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])C.CC(C)([O-])C.[K+].O.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[C:10]([O:9][C:7]([N:6]1[CH2:14][C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[NH:22][C:4](=[O:3])[CH2:5]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

参加物

7

反応物 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 67364561HCID 67364561、化合物

生成物 1

HCID 67377785tert-Butyl 7-chloro-2-oxo-1,2,3,5-tetrahydro-4H-1,4-benzodiazepine-4-carboxylate収率 88%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of [(2-amino-5-chloro-benzyl)-tert-butoxycarbonyl-amino]-acetic acid ethyl ester (60 g, 0.18 mol) in tetrahydrofuran (600 ml) was added potassium tert-butoxide (22 g, 0.19 mol) in small portions at 5° C. under cooling on an ice-water batch. After completed addition the cooling bath was removed and reaction mixture was stirred for 3 h at room temperature followed by addition of water (400 ml), saturated aqueous ammonium chloride solution (280 ml) and ethyl acetate (800 ml). After 10 min the precipitate was collected by filtration. The layers were separated from the filtrate, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was combined with the precipitate, which had previously been collected by filtration, and crystallized from hot ethyl acetate to give the title compound (46 g, 88%) as white solid. MS m/e: 295 (M−H+).

後処理

  1. additionaddition the cooling bath
  2. customwas removed
  3. customreaction mixture
  4. filtrationAfter 10 min the precipitate was collected by filtration
  5. customThe layers were separated from the filtrate
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. filtrationhad previously been collected by filtration
  9. customcrystallized from hot ethyl acetate

出典と根拠

ORDレコード
ord-133420fb68cd467b96c42b6d1ef4515b
出典データセット
uspto-grants-2014_02
特許番号
US08642590B2

反応ノート

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